sailboat charter in caribbean

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Find Caribbean Crewed Yachts for the Vacation of a Lifetime

The Caribbean is one of the most popular destinations for yacht charters in the world, featuring crystal-blue waters, white-sand beaches, and more than 5,000 islands and cays to explore. With so many islands to choose from, your Caribbean yacht charter itinerary can be tailored to your preferences, giving you the perfect opportunity to island-hop and explore everything the tropical islands have to offer while comfortably kicking back inside luxurious accommodations on the water.

On your private yacht charter , you will be able to explore lively harbors, secluded beaches, tropical rainforests, world-class dive sites, and much more. The possibilities are endless!

Caribbean Yacht Charter Highlights

• More than 5,000 islands and cays to explore
• A great winter destination
• Crystal-clear, sparkling blue waters
• Long stretches of white-sand beaches
• Luxury hotels, five-star restaurants, and spas
• Islands with their own unique cultures and cuisines
• A large selection of crewed yachts for charter

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282.2ft / 84m

239.6ft / 71m

228.6ft / 68m

223.7ft / 67m

Caribbean Yachting Season

The Caribbean high season for yacht charters runs from mid-December to early May, with Christmas and New Year’s the most popular and busiest times of the year. But due to the islands’ locations near the equator, temperatures remain ideal throughout the year, making off-season charters just as enjoyable.

Keep in mind, however, that there is an increased chance for storms and hurricanes during the summer season, mainly from mid-August to mid-November. Most charter yachts leave the area during that time.

Caribbean Crewed Motor Yacht Charters

Remember When

162ft / 48m

Sweet Escape

130ft / 39m

116ft / 34m

Caribbean Catamaran Charters

105ft / 31m

Serenity Now

Caribbean Crewed Sailing Yacht Charters

Area Guide: Caribbean Charter Destinations

Are you ready to explore all that the Caribbean has to offer? There are three main island areas in the Caribbean, all fantastic destinations for Caribbean charter yacht vacations.

The Grenadines

The Grenadines are untouched by mass tourism and industry, and they are the perfect charter destination if you are looking for solitude and you enjoy exploring remote areas. A great combination of lush rain forests and sandy beaches awaits!

This is a great summer charter destination because the islands aren’t usually affected by hurricanes.

The Leeward Islands

Leeward Islands yacht rentals offer the perfect combination of luxury and solitude. You can visit the glitzy islands of St. Maarten and St. Barts one day and get lost in the remoteness and tranquility of Anguilla the next day.

These islands are rich in history and offer great restaurants, upscale resorts, and trendy harbors.

The Virgin Islands

The Virgin Islands are the perfect location for first-time charterers and families because of their calm waters, protected natural anchorages, and short distances between the islands.

The BVI are a great destination for a catamaran or sailing yacht charter. Caribbean locations here have constant yet mild trade winds year round, and the area offers fantastic diving and snorkeling.

Where Can I Charter a Yacht?

When you choose Worldwide Boat as your Caribbean yacht charter broker, we can help you charter a luxury boat anywhere in the Caribbean or anywhere else you’d like to go, from the Mediterranean to Alaska to the Galapagos Islands.

How Do I Book a Private Yacht?

The best Caribbean yacht charters can be booked in just a few easy steps:

• Choose our experienced yacht charter specialists to assist you through the process of booking a yacht.
• Search by destination or by boat, or use our advanced search tool to filter your options by the number of guests, yacht type, destination, and/or your budget.
• Pick the option that best fits your needs and your dream vacation.
• Reserve your yacht by signing a contract with the yacht owner.
• Enjoy your vacation!

How Much Does it Cost to Charter a Yacht in the Caribbean?

Weekly rates for Caribbean boat charters are dependent on a number of factors, including the type of yacht, the season, and your destination. Motor yachts, for example, typically range from $15,000 (yachts up to 80 feet) to $150,000 or more (yachts over 150 feet) per week.

During the Caribbean high season (Christmas, New Year’s, and January/February), yacht charter Caribbean prices tend to increase slightly. Areas with large charter fleets, like St. Martin, tend to have more competitive pricing than areas with smaller fleets.

How Much Does it Cost to Charter a Catamaran in the Caribbean?

Most catamarans offer all-inclusive rates, which start at $10,000 for catamarans under 50 feet and run up to $50,000 or more for catamarans of 80 feet or more. The Caribbean is an ideal destination for a catamaran charter, and across the region, you’ll find a variety of sailing and power cats available for charter.

Ultimately, the cost of a catamaran charter is dependent on the time you visit, where you go, local taxes, and the number of ports you visit. A luxury yacht charter in the Caribbean’s high season (New Year’s or Christmas) will cost significantly more than a catamaran charter in summer.

Can I Rent a Yacht for a Day?

Rates for yacht rentals are usually weekly, but when you talk to a Caribbean yacht charter broker at Worldwide Boat, we can look at your budget, plans, and interests to help you get the best experience possible.

Caribbean Yachting Hotspots

Caribbean sailing charters give you access to white-sand beaches and laid-back island vibes, but they can also offer action-packed itineraries. From island-hopping and hiking to snorkeling and cliff-jumping, adventure awaits on a Caribbean yacht charter!

Some of the region’s must-see destinations include:

• St. Martin : Known for its upscale eateries and amazing cuisine, as well as high-end spas, shopping and casinos, St. Martin is the yachting capital of the Caribbean. This island is part French and part Dutch, and it’s close to islands like St. Barts and Anguilla, making it a favorite jumping-off point for island-hopping adventures.
• St. Barts : St. Barts (sometimes called St. Barths) beckons A-listers to its posh beach clubs, fashionable shops, and five-star eateries. Visitors will find a collection of truly spectacular powdery beaches, Michelin-starred restaurants, and excellent shoreside amenities, all within cruising distance of St. Martin.
• Antigua : Antigua epitomizes the relaxation and bliss of the Caribbean. Known for its 365 beaches (one for every day of the year), the tiny island is a sailor’s dream, offering warm waters, steady winds, safe anchorages, and a lively regatta calendar.
• Grenada : Grenada is revered for its beautiful beaches, abundant marine wildlife, and vibrant cuisine (spiced with local nutmeg, mace, and allspice). Spend a day relaxing on Grand Anse Beach, which is consistently ranked one of the best in the world. Island-hop to neighboring isles like Petite Martinique, or spend a day snorkeling one of Grenada’s famous reefs.
• Anguilla : Anguilla is one of the most tranquil Leeward islands. Escape to Dream Bay or one of the numerous nearby coral cays for some supreme R&R. A diving and snorkeling mecca, Anguilla is home to some of the Caribbean’s best shipwreck dives. Plus, the island boasts a calendar of must-see festivals and events, including a jazz festival in November and Carnival in August.

Why Charter a Yacht in the Caribbean?

The best Caribbean yacht charters offer a bit of everything: Relaxation, sun-soaked beaches, delicious culinary treats, refreshing rum-infused cocktails, and calm waters for cruising. Here are some highlights:

The Inescapable Beauty of White-Sand Beaches

Caribbean beaches have almost a mythical quality to them. It’s no wonder explorers were once willing to board wooden ships and travel thousands of miles just to see them in person.

Every island offers a selection of untouched and charming beaches for you to explore. From one-of-a-kind places like “Pig Beach” in the Bahamas to the cosmopolitan Great Bay Beach in Philipsburg, St. Martin, the beaches across the Caribbean offer legendary sights and attractions.

Colorful Celebrations and Friendly Faces

The Caribbean is known for its parades, bars, nightclubs, and parties, not to mention world-famous cocktails. When you want to step off of your luxury yacht charter, Caribbean shores and islands offer a world of fun to immerse yourself in.

A few must-see events include the St. Barth’s Bucket (if you’re into superyacht racing), the annual Carnival celebration, and the St. Lucia Jazz & Arts Festival .

Amazing Wildlife and Adventure

If snorkeling in vibrant and colorful coral reefs, diving into underwater museums, or parasailing over clear waters are some of the items on your bucket list, you can certainly get it all done during your visit to the Caribbean.

You’ll find a variety of unique adventures, from the underwater sculpture park of the Grenadines to the natural seaside baths in Virgin Gorda and hiking the Pitons in St. Lucia. The Caribbean gives you to plenty of chances to get outside and enjoy yourself.

Nonstop Relaxation

Because the area is so close to the equator, the Caribbean offers warm weather to lounge in all year round. Feel pampered aboard a luxury crewed rental yacht, and then feel calm while sinking your toes into soft, powdery white sand. Enjoy the spas, rum cocktails, and quiet, isolated beaches: Charter guests can experience supreme relaxation in the Caribbean.

Book Your Caribbean Charter With Worldwide Boat

Discover the beauty of the Caribbean with a luxury crewed yacht charter. Contact a broker with Worldwide Boat today to learn more about available yachts and itineraries for the Caribbean.

Last edited by Katja Kukovic

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Find Your Perfect Yacht

Caribbean yacht charters - one resource for every luxury charter yacht

The proven resource for crewed yacht charter in the caribbean.

From the moment you contact us, you will be helped by an experienced and knowledgeable specialist who will take the time to understand your unique needs and preferences for your caribbean vacation. They will be your dedicated specialist and our exceptional personal service will answer every question.

The largest choice of crewed Caribbean yachts?

Absolutely, with our relationships built over decades we truly do have access to EVERY crewed private charter yacht based in, or visiting, every part of the Caribbean.

Whatever the type of yacht for your Caribbean charter, your vacation budget, or the size of your party, our specialists will guide you in choosing the ideal yacht for your Caribbean charter. It's your vacation to explore the islands the very best way possible - on a Caribbean charter yacht.

Browse different types of Charter Yachts in the Caribbean

Motor Yachts

This category of Caribbean yachts include mega yachts, super yachts, and all sizes of power yachts. With the maximum space for guests, both inside and out, these types of yachts offer excellent vacations. You can choose from a fast, agile yacht, one that is high-end and luxurious, a yacht with a classic design, or one that is contemporary. This is one of the many choices you’ll have when you plan your vacation. See some yachts:-

Crewed Catamarans are very popular in the Caribbean , especially in the BVIs. Catamarans offer ample deck space that allows everyone to relax together during their charter, sharing the same views throughout the voyage. Caribbean catamarans can typically accommodate between 6 and 12 guests. See some yachts:-

Sailing Yachts

If you are looking for a winter getaway, there is no better place to charter a sailing yacht than the Caribbean! Feel the warm, tropical breeze on your face. Experience the exhilaration as the wind fills the sails and the yacht is suddenly moved along by just the wind. Savor the magnificent beauty of the Caribbean as you sail silently from one island to the next. Although typically offering smaller spaces for guests, sailboats deliver a truly unique caribbean charter vacations . See some yachts:-

Sample Charter Yachts in the Caribbean

ODYSSEA. The 59' sailing catamaran Odyssea is ready to take you and your guests on your next adventure. Throughout she offers relaxing areas to lounge and enjoy the voyage, while enjoying the company of others or absorbing the serenity of the sea. Her spacious cockpit area offers large dining table, sun pad across the back, and wet bar. See ODYSSEA :-

OKTO. Get ready for adventure when you step on board the 217' mega yacht Okto. You and your guests will find plenty to do, as she offers plentiful spaces for lying out to enjoy the sun, enjoying a movie in the circular cinema, working out in the indoor gym with an amazing view, or enjoying the on deck Jacuzzi. See OKTO :-

NAMASTE. The immaculately maintained mega yacht Namaste offers 121 feet of opulence at sea. She features five well-appointed cabins, both a main salon and sky lounge, sundeck with Jacuzzi, gym equipment, and a long list of watersports including jet skis, wakeboard, fishing gear, and the list goes on. See NAMASTE:-

NENNE. The 67' sailing catamaran Nenne was launched in 2017 by Fountaine Pajot, and was given a refit in 2020. With five cabins, she accommodates as many as ten guests, and has an impressive list of water toys that includes water skis for adults and children, wakeboard, standup paddleboards, fishing gear, snorkeling equipment, and the list goes on. See NENNE:-

MARIAH PRINCESS III. The 77' Lagoon built sailing cat Mariah Princess III was built in 2020. She offers two queen cabins and two king cabins, all en-suite. The master cabin has a private deck, the flybridge offers an on deck Jacuzzi, and she has a generous complement of watersports, including onboard SCUBA. See MARIAH PRINCESS III:-

TRUE STORY. The 67' sailing catamaran True Story is ready to give you and your guests a fun and exciting charter in the beautiful waters of the Caribbean. She offers a spacious main salon, large cockpit with al fresco dining and lounge, and flybridge with conversational area. You and your guests can also enjoy a long list of water toys throughout your journey. See TRUE STORY:-

The British Virgin Islands include Tortola, Jost Van Dyke, Virgin Gorda, and more. There’s no better way to experience the waters and beaches of the BVI's than on a private Caribbean charter with a full crew to pamper you. Of all the islands in the Caribbean, the Virgins are furthest north. This makes them very convenient due to the proximity to San Juan and due to their direct flights from the United States. Catamaran sailing vacations and crewed sailing charters are very popular in the islands, and their protected waters make them a favorite spot for guests that are taking their first private Caribbean yacht charter. To learn more about them:

The U.S. Virgin Islands consist mainly of the three large islands of St. Thomas, St. Croix, and St. John. With lovely bays, long beaches, lush nature preserves, fabulous diving spots, and excellent, onshore evening entertainment, many choose to vacation in the USVI’s. Caribbean charters often visit both the BVI’s and USVI’s during the same week, as they are close to one another and the waters are generally calmer than in other parts of the Caribbean. They in general are also home to the largest fleet of crewed, all-inclusive, luxury catamarans. To find out more about them:

The Leewards are situated in the middle of the Caribbean Island chain. The major airports are located on St. Maarten and Antigua. Due to the English, Dutch, and French influences everywhere you look, they exhibit the best example of cultural sophistication anywhere within the Caribbean. If you are looking to see where the rich and famous go on vacation, you will want to visit the island of St. Barts; for many this is a must stop for a Caribbean yacht charter. Many mega yachts are available for rental in St. Maarten, as it has become a popular mega yacht Caribbean base for the winter. To learn more about the Leewards:

The Grenadines are also called The Windward Islands. Oftentimes our guests will choose a sailing charter over a motor yacht when in the Grenadines, due to the more constant tropical breezes that occur. The islands are much less developed than the rest of the Caribbean, and the inhabitants live on their own time schedule, which enhances the feeling of getting away. The northern most island accessible by air is ST. Vincent, while the southern tip’s major airport is on Grenada. There are fewer Caribbean charter yachts based here; however, occasionally some charter yachts are happy to relocate in order to offer a vacation that happens a little off the beaten path. To find out more about the Grenadines:

What Type of Charter Yacht?

There are all types of Caribbean yacht charters available, including mega yachts, power yachts, catamarans, and sailboats. We have helped countless clients choose the right charter yacht, learning what features and amenities make a difference on caribbean charter yachts. Learn more about different types of Caribbean yachts.

Where Can You Go?

Typically you’ll choose between the Virgins, Leewards, and the Grenadines to charter your yacht. Beyond the region, it is your Caribbean to explore. It’s important for you to remember that there is no cruise ship itinerary to worry about! Your itinerary will be custom designed specifically for you, with you, and is flexible to changes during your charter. We have put together some samples for you to get an idea of what you might like to do while on vacation in the Caribbean. Interested in seeing a sample cruise itinerary ?

Find Your Perfect Yacht for a Caribbean yacht charter

To see the Caribbean yachts we have in our online database, please select a yacht type and your budget below. Please keep in mind that we do not have every available yacht online. There are many more yachts available for you to choose from when you contact one of our specialists.

For your personalized selection including yachts not online:- Email us now

Caribbean Charters - When To Go.

One of the lovely things about the Caribbean is that the temperatures remain consistent throughout the year; however, there are some other weather considerations that you will want to factor in when making your caribbean yachting vacation plans. Read More....

Vacations here are most popular between November and July.

If you are thinking of a megayacht, you will want to keep in mind that many of these private yachts which are Caribbean based in winter leave in the late spring and early summer months. They will return again in early winter; however, this does limit their availability. To charter a mega yacht, you will want to make sure that you do so well in advance.

Motor, sail, or catamaran yachts, on the other hand, often have selections available year round. Holidays like Christmas, New Year’s, and Easter do need to be planned for as early as possible as these are very popular charter times.

The availability for Caribbean charters can also be affected by the weather in other climates, for instance, when the severity of the weather is bad in the United States or Europe, especially between January and February, the charters are often booked. This is due to many clients looking for a break from the cold.

What Do Our Clients Say About The Caribbean?

Are you excited yet? You should be! Our clients have enjoyed fantastic Caribbean vacations. There is an endless number of places to visit in the Caribbean, from smaller islands to absolutely must be seen locations like St. Barts. Read some of our Caribbean charter reviews from clients who booked a Caribbean charter with us.

Ready to learn more about Caribbean charters?

We are specialists who will make your trip a reflection of our expertise! We know clients need to be confident in their charter vacation plans, so we encourage our clients to benefit from the knowledge base we’ve been building for years. You’ll speak to an authority on Caribbean charters without any obligation on your end.

Test our expertise with your questions!

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CARIBBEAN YACHT CHARTERS

Caribbean yacht charters, is synonym to tropical paradise and an excellent sailing destination. White sandy beaches, clear waters and palm trees make Caribbean bareboat charter an unforgettable sailing experience. Islands surrounded by the Atlantic Ocean and Caribbean sea, provide numerous destinations.

Rent a Boat in Caribbean: 1321 Available

Robertson caine 51 pc power boat charter (2015).

Rent a boat Oceanis 43 (2009) in Grenada

Sailboat Dufour 412 GL (2018) for rent in Antigua

Dufour 412 GL sailboat charter (2018)

Rent a boat Dufour 390 GL (2019) in Guadeloupe

Sailboat Dufour 425 GL (2012) for rent in Antigua

Dufour 460 GL sailboat charter (2018)

Rent a boat Dufour 460 GL (2018) in Guadeloupe

Sailboat Dufour 390 GL (2019) for rent in Antigua

Oceanis 41.1 sailboat charter (2018)

Caribbean Yacht Charter Reviews with 12knots

United States

“Excellent charter”

Excellent charter - I recommend them!

YACHT CHARTERS

Charlie Clarke

United Kingdom

“We had a lovely time and the boat was really easy to handle”

Grigory, we had a lovely time and the boat was really easy to handle and only about 5 months old. All the equipment was in really good order and everything worked without a hitch. We had a really good handover from Nomicos who got us through the chec…

Michael Zulla

“Private charter with 12 Knots”

Our week-long private charter with 12 Knots on a Bali 46.5 catamaran was a remarkable experience. Sailing through Sardinia and Corsica was made even more enjoyable by our capable and friendly crew. And the team at 12 Knots planned a wonderful itinera…

Alberto Goosen

“Thank you and your team so much for arranging everything”

Dear Grigory, I have been wanting to write you since I got back. Thank you and your team so much for arranging everything. Everything turned out as planned and we had an unforgettable trip! There were some unexpected surprises along the way…. but tha…

Flori Grottoli

“Spanish Virgin Islands are stunning / March 2019 / Puerto Rico / Dufour 412”

The experience was beautiful and the Spanish Virgin Islands are stunning! Even though we started off with a few setbacks (had to switch boats because of technical issues), the marina made good and was very accommodating....they did the very best they…

“Our trip was fantastic!”

Our trip was fantastic, beyond expectations. Our skipper, Peter Papageorgiou, was the best, also.

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Sailing Around Windward and Leeward Islands of the Caribbean

The  Caribbean covers a huge region of widely spread islands 2,000 miles (3,218 km) long.

The larger ones have become sovereign countries with broad range of amenities for sailors, while the smaller ones still preserve its untouched rural charm and tranquility.

From the western tip of Cuba to the Leewards in the east, then south to the top of South America and along Venezuela’s north coast – this chain of islands has created a hook-like shape around the Caribbean Sea. Location like this is always an enticing bait for sailing - perfect climate and  array of diverse cultures, customs, cuisines and experiences, water sports and an unlimited number of other attractions.

Planning sailing vacations in Caribbean, you may wish to consider these groupings of the islands as points of your itinerary, as they contain many popular cruising areas and harbor stops. There is no doubt that in the scope of Caribbean bareboat or skippered yacht charters  both groups have their charms and countless reasons to explore, which definitely makes it a great sailing destination.

Caribbean yacht rentals

12 Knots offers eleven yacht charter bases in the Caribbean region, each with unique individual character, providing sailing experience for everyone, from a novice to an experienced sailor. This region comprises more than 700 hundred islands and islets, so you can choose Caribbean sailing vacations with shot and easy hops or more challenging passages.

Taking Caribbean sailing vacations, you will find warm and steady trade winds in picturesque surroundings; discover plenty of great bars and authentic cuisine!

It’s up to you, choosing between the Leeward Caribbean islands with short and easy hops with line-of-sight sailing and the Windward with more challenging open water passages. Wherever you go, you will return home relaxed, refreshed and ready to start planning your next Caribbean sailing adventure.

The Windward islands

Windward Islands located at the southern end of the Caribbean island chain and stretch for over 300 miles to the south-eastern end of the Caribbean Sea. The Windward Islands are simply called so due to their position as they are exposed to the northeast trade winds. For experienced sailors, it can be right choice to sail among the four main islands: Martinique, St. Lucia, St. Vincent and Grenada. They lay far apart each other allowing open ocean sailing and while steady easterly trade winds, make passages north or south easy. With constant 12 to 25 knots wind, Caribbean sailing is among best in the world. Night anchorages in peaceful and protected areas give sailors freedom to explore and soak up British and French island culture. The islands of St. Lucia, St. Vincent and Grenada  were British colonies until they gained independence during the 1970s. Martinique is still an overseas department of France.

The climate of the Windward Islands is definitely a marine one.

When tropical heat reaches its peak, steady trade winds and daily sea breezes come to rescue.

Typically, dry and wet seasons go hand in hand here. Although the priority of more rainfalls is given to the eastern side of the islands mainly due to the prevailing north-east trade winds there.

The islands east of Puerto Rico were called “Windward Islands” by the Spanish, while the islands south of Puerto Rico were named as “Leewards “. And Dominica positions itself right on the border line between the Windward and the Leeward Islands.

Long time ago some of the islands used to be French colonies, subsequently gained its name as The French Antilles.

The population of the Windward Islands is mostly of African origin, with some exceptions of Chinese and Caucasians. The present day Windward Islands will welcome tourists with upscale resorts, stunning beaches and pleasant sunny weather.

After cruising through the Windward Islands, you may wish to set sails to the Leeward Islands.

The Leeward islands

The Leeward islands are located on the eastern edge of the Caribbean Sea and form the northeastern boundary between Caribbean and Atlantic Ocean, extending from Puerto Rico to the Windward Islands, forming part of the Lesser Antilles chain.

Although 700 miles long stretch of these magnificent isles mostly constitute the whole body of the Leewards, it provides the abundance of enjoyment: quaint fishing spots, ancient ruins and delicious authentic cuisine.

Blessed with balmy temperatures all around the year, The Leeward Islands are called leeward because they're away from the wind or downwind (in the "lee"). Leeward group of Caribbean islands includes: the U.S. Virgin Islands, the British Virgin Islands, Anguilla, Saint Martin, Saint-Barthelemy, Saba, Sint Eustatius, Saint Kitts, Nevis, Barbuda, Antiqua, Redonda, Montserrat and Guadeloupe.

One of two "sister islands", St Kitts and Nevis, provides a brilliant Caribbean experience, from their picture-perfect beaches and volcanic mountains to friendly locals and layers of history to explore. For the water sport lovers, there are numerous aquatic activities that include fishing, diving, windsurfing and surfing.

St.Kitts and Nevis

Switch from sailing to inland for a change and St.Kitts and Nevis will deliver the most exceptional hiking in the Caribbean. The dormant volcano of Mount Liamuiga is considered to be the toughest to climb. And with the experienced guide you may even try to descend in its crater!

The unspoiled landscape of dry littoral forest and rainforest will present memorable show of fauna and flora. Many plants are of culinary and medical use, and some even used in black magic, as informative guides would point out its botanical value.

The wild life-lovers will not be disappointed with variety of different types of exotic animals.

Actually, the Great Salt Pond has become famous for its largest habitat of green velvet monkeys.

St. Kitts and Nevis will keep you captivated with majestic view of huge conical shells, remains of old sugar mills, along with some other plantation ruins, built in the 18 th century.

Back to water activities, and tourists will be pleased with what these two island can offer: deep-water fishing, snorkeling, scuba diving and more.

Then in order to satisfy your growing appetite visit two popular restaurants: Carambola and the Shipwreck Bar and Grill to enjoy its delicious local meals.

A yacht charter in the Caribbean Leeward Islands offers sailors an unrivalled remarkable experience. Enjoy tropical landscapes, pristine palm-lined beaches and azure waters — all the joys of marine life.

Sailing over the Leeward Islands may have all the pleasures to offer: the Tropical rainforests, glittering coral reefs, and luxury sand beaches. That’s probably why most of the known tourist resorts on these islands play a critical role in their economy, as do banking and fishing. Many of them also rely on their status as a tax haven to promote offshore financial services as a source of government revenue. But there is much more to discover in the Leeward Islands. These Caribbean islands provide great variety of yachts for charter and pleasant sailing vacations. Most of the Leeward Islands are located close to each other with moderate winds from 10 to 15 knots and rather low wavers. BVI is the most popular area for Caribbean charters either bareboat or luxury crewed vacations. This is the right place for the novice sailor’s easy passages in line-of-sight sailing.

The climate of the Caribbean Leeward Islands can be described as tropical, but much drier than in Windward Islands. Though the climate does vary from island to island and can even be different in different parts of the same island. Rainfall increases with elevation and in more southerly latitudes. In some cases trade winds look like refreshing tonic to the tropical heat. There is minor seasonal variation, although the second half of the year, the wet season, is slightly warmer and rainier. The best time for sailing in the Caribbean may be the first half of the year. At this time the temperatures usually range between 81°F (27°C) and 95°F(35°C). Annual rainfall averages about 40 to 50 inches (1016 to 1270 mm). Keep in mind, that nearly every island had been severely damaged by hurricane activity in its recent history.

English is the most widespread language all around the islands, plus many of the people speak French and Dutch on the St Martin Island. Both English-based and French-based Creole are also spoken. The prevailing currency is The East Caribbean dollar. But St Martin is odd man out again, circulating the Netherlands Antilles guilder in the Dutch area and the Euro in the French region. Nevertheless, the US dollar is widely accepted throughout the islands.

If you eager to take part in sporting activities, then you may be pleased to know that cricket is widely played and followed in the former British territories. Besides, as in the rest of the Caribbean, music is also always a big part of local life. Enjoy the magical sounds of calypso, soca, steelpan, reggae, salsa and jazz — all of the mentioned has their adherents.

During your Caribbean yacht charter, you may wish to participate in some major holiday celebrations, including the St Kitts Christmas, New Year carnaval, the annual music festival, as well as Anguilla’s Emancipation Day and Culturama festival on August 1st.

The culture of the Leeward Islands is varied by different influences, including French, Dutch and West Indian. Due to that sailing around the Leeward Islands provides a wonderful choice of cuisine and some great restaurants to satisfy your affection for the finest dishes. By the way, the island of Anguilla offers true gastronomic feasts. When sailing in the Caribbean Leeward Islands, be sure to try freshly caught lobsters with a glass of wine.

Sailing the Caribbean With 12 Knots

So, while planning a Caribbean charter it is highly recommended to decide on how many islands you would like to visit in a given time frame. Research Caribbean boat rentals and determine which island you would like to have as a starting base. Then you can plan an itinerary for the week or ten days, taking into consideration distances between the islands and activities you would like to have, like island tracking, scuba diving, snorkeling, volcano hiking, or even shopping.

12 Knots team will give you plenty of useful information not only on the bareboat charter in Caribbean, but also itineraries, places of interest and peculiarities of each island.

Taking a yacht charter in the Caribbean is just a perfect combination of sailing and relaxation, authentic culture and a range of water sport activities. In a few words, this area may always offer something for everyone in these amazing islands’ surrounding.

Frequently Asked Questions about yachting in Caribbean

How much does it cost to rent a yacht in caribbean , how many boats are available for rent in caribbean , what are the main yacht charter bases in caribbean , what boats are available for charter in caribbean .

Caribbean Yacht Charters

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Featured Yachts in THE CARIBBEAN

LADY JOY | From US$ 199,000/wk

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• Caribbean Yacht Charter

Perhaps the best tropical yacht charter spot worldwide, there are over 700 islands to choose from in the Caribbean. However, Caribbean yacht charters can be split into two main area: the Greater Antilles and the Lesser Antilles. The Greater Antilles is home to countries like the Dominican Republic, Jamaica and Cuba while the Lesser Antilles can be subdivided into the Windward and Leeward Islands. The Leeward islands include St Kitts and Nevis, the British Virgin Islands, Anguilla along with Antigua and Barbuda. The Windward Islands comprise the Grenadines, Grenada, Barbados, Dominica, St Vincent and St Lucia.

ALFA NERO | From EUR€ 812,000/wk

Maltese falcon | from eur€ 480,000/wk, seven sins | from eur€ 270,000/wk, g2 | from us$ 85,000/wk.

Sailing Yachts Under 100' - Sailing Yachts Over 100' - Motor Yachts Under 100' - Motor Yachts Over 100' - Catamarans Over 50'

The stunning and diverse Caribbean beckons travelers back year after year. With its beautiful climate, fantastic coral reefs, palm trees and exotic tropical islands, there are lots of reasons to make this your next sailing destination. Don’t forget the rum cocktails either! As the second largest yachting area, only after the Mediterranean, there are many luxury yachts available for your Caribbean yacht charter and you can view some of the yachts below or here .

Reviews of Caribbean Charter Vacations | Caribbean Holiday Fact File | Top Caribbean Spots | Sample Itinerary | Charter Yachts Available

The Bahamas and Turks and Caicos are not really in the Caribbean although are known as superyacht destinations in the Caribbean. Wherever you decide to charter a luxury superyacht in the Caribbean you will enjoy a totally relaxing vacation and beautiful scenery.

How Much Does it Cost To Charter in The Caribbean?

Caribbean yacht charter prices vary according to the size, style and age of the yacht you rent. Our luxury superyacht charters rent from 30,000 USD to over 1,000,000 per week, plus expenses, in the form of an advanced provisioning allowance (APA). Conversely, smaller 'all inclusive' type vacations cost between USD 15,000 to 50,000 per week. View the list of yachts and prices here .

Experience the luxury of Crewed Private Yachts in the Caribbean

A traditional hot spot for crewed charters, the Caribbean is considered “the king of yachting vacations”, so please contact us here to go on your private charter. Whether you agree with this or not, you like most people will have heard of the Caribbean as a great yacht charter destination. This is because this location covers a huge area and offer fantastic diversity. It is beautiful and warm, has amazing beaches, interesting cultures and perhaps most importantly, the Caribbean has a huge selection of crewed yachts, luxury yachts and superyachts which you can rent and experience a truly magnificent vacation around the various Island groups. The Caribbean is a natural wonderland onshore, but probably most importantly, it has an ocean laden with treasures, from tiny beach ridden coral atolls to substantial mountainous islands exuding rich and colorful cultures. An area which is famous for its beautiful waterways and islands, there is no better way to experience the Caribbean than on a crewed luxury yacht vacation.

Some of the Recommended Caribbean Yacht Spots:

Popular places to visit on a yacht include Antigua , St Barts , Anguilla , St Martin , The British Virgin Islands , The US Virgin Islands , the Grenadines and many more – see more below.

More than ever crewed luxury yachts are beginning to explore more exotic and remote Caribbean Islands, so ask your charter broker or captain for more information on some of these more remote treasures. Due to the scale and diversity of the different areas of the Caribbean we have covered the major charter locations individually. Please note that if there is a charter boat cruising area, not covered here that you are interested in, please contact us and we will provide you with that information personally in the form of a yacht charter itinerary.

As one of the most popular locations in the world, second only to the Mediterranean in popularity, the types of boats available for rental in the Caribbean include all the main types such as motor, sailing, skippered, crewed yachts, catamarans, power boats, sailboat, luxury yachts as well as the ever growing superyacht and mega yachts. Both beginner and experts alike are drawn to the Caribbean for its warm winds, protected waterways and beautiful anchorages. The Caribbean is a special place that has beautiful tropical islands that lie snug within a tropical island necklace as laid out on a large blue sea.

The Caribbean is also steeped in a fertile history of sailing adventure. Ever since the days of galleons and pirates the Caribbean has been host to some of the most satisfying sailing anywhere in the world. On your Caribbean yachting vacation you can find, an incredible amount of choice and variety and all in a relatively small area - thriving bars and Caribbean nightlife; first rate cuisine; spectacular white powder beaches; lush tropical rain forest; cloud-fringed mountain peaks; exotic bird life; amazing diving and snorkeling and a serene blend of European sophistication and warm Caribbean hospitality. The problem is, with so many superb Caribbean yachting locations and charter boats to choose form, where do you start when planning a holiday? With CharterWorld of course…

The Time of Year to Charter a Yacht in the Caribbean:

The main Caribbean sailing season runs from November through to July. The Caribbean primary high season is from mid-December to March, when the winter escapees from North America and Europe arrive in their greatest numbers. The hurricane season is from late July to early October, although hurricanes are in general rare in the southern Caribbean. Unfortunately, they can be prevalent around Cuba, Bahamas and the east coast of the U.S. every few years. This is the least expensive time for chartering in the Caribbean and there are some really good deals are available. However, as well as running the risk of storms, this time of year also tends to be associated with lighter (or non-existent) winds.

As with many boating locations the Caribbean shoulder season, in this case from April to July, is also a great time to charter a boat as there are less shore based visitors, some lovely settled sunny weather, and warm yet steady breeze. The Caribbean is made up of many different multi-nation (and multi-cultural) volcanic islands. There are amazing sailing grounds stretching from Cuba and Jamaica in the west, through the Dominican Republic, Puerto Rico, The Virgin Islands, The Leeward Islands and the Windward Islands, finishing with Trinidad and Tobago off the coast of Venezuela.

Caribbean Yachting Hot Spots:

Here is a brief list of some of the Caribbean hot spots to consider experiencing when you rent a luxury crewed charter yacht. This is by no means an extensive list and there is more information on things to see and do in the Caribbean under each Caribbean private yacht location. Also, when you hire a yacht with us we will supply you with a customised hand written itinerary suggestion so that you and your crew have a few ideas to choose from on your charter.

General Places/Events Worthy of Experiencing:

- Gustavia Harbour in St Barts - shopping, nightlife, restaurants and European quintessence - Nelson in Dockyards in Antigua - history and beauty in a harbour - Sunset in St Lucia - St Kitts for the beauty, history and magnificent views from Brimstone Hill Fortress - Anegada for its deserted beaches, fringed reefs and the unique flora and fauna of the salt ponds, home to the pink flamingo - The BVIs for the beautiful beaches and anchorages - Guadeloupe for its diversity - one side offers cosmopolitan flair, bordered by beaches and coral reefs and the other has open lands with the fertile, volcanic peaks , rain forest and waterfalls.

How to get to the Caribbean

There are direct flights from the UK and the US to Barbados, Jamaica, St Lucia and Antigua. Some Caribbean islands require a connecting flight as they have small airports which cannot handle large aeroplanes. Across the Caribbean, many islands have private jet facilities with fantastic runways.

What is the currency in the Caribbean?

Various currencies are used in the Caribbean. For instance, in Anguilla, Dominica, Grenada, St Kitts and Nevis, St Lucia, St Vincent, the Grenadines and Antigua, the East Caribbean dollar is the currency. Jamaica, Barbados, the Cayman Islands and the Bahamas have their very own currency. US dollars are accepted on most of the islands however the ATMs tend to have only the local currency.

Language spoken

There are four main languages spoken in the Caribbean, French, Spanish, Dutch and English. English is the first or second language and is mostly used when tourists visit. The official language of Haiti is Haitian Creole while Papiamento is used in Curacao, Bonaire and Aruba. Different creoles and local patois are also spoken on the various islands.

Time Zone in the Caribbean

Two time zones are used in the Caribbean. GMT -5 and GMT -4. Daylight saving time is implemented in many countries including Bermuda, Cuba, Haiti, the Bahamas including the Turks and Caicos Islands.

Visas and customs immigration

British and American tourists do not need visas if they are staying in the Caribbean for less than 90 days. It’s advisable to check the exact requirements for the countries you intend visiting. American tourists are still not allowed to visit Cuba although this may change in the future.

What to consider medical/health wise when chartering a superyacht in the Caribbean

There aren’t any extra medical issues for travelers in the Caribbean but check with your travel agent for any current warnings. The most common are complications form insect bites, jelly fish stings, cuts from coral and heart-related illnesses.

Short List of Caribbean Sailing Yacht Events:

- Antigua Sailing Week – held during the last week of April each year, yachts from all over the world arrive in English and Falmouth Harbours for an action packed week on fun sailing. - St Bart’s Bucket - Grenada Sailing Festival - Heineken Regatta – a Caribbean sailing and party Regatta – The Heineken St Maartens. - Here is the full list of Caribbean yachting and sailing events.

Other Caribbean Places to be:

- New Year’s Eve at St Barts Gustavia, St Martin and the BVI's - More info on Caribbean yachting and sailing events - Please see the Specific Caribbean location links on the left for more.

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CARIBBEAN Yacht Charter Enquiry

Trina, Everything was perfect! The yacht, the crew, activities... The crew in particular was off the charts! They really did go out of their way to please us. Please release the full amount of the gratuity. I have nothing but good things to talk about the charter, an opinion shared amongst all of the guests. Thank you for all your help with the charter of Miracle, everything went smoothly and you were very professional and efficient during the whole process. I will not hesitate in contacting you for our next charter (next year, hopefully!!). Miracle BVI's charter (british Virgin Islands) Caribbean in April

Yachting Destinations Near the Caribbean

Explore Location Guides for great destinations near the Caribbean .

Jost Van Dyke

Yachts for Charter in the Caribbean

112m freire superyacht | from eur€ 3,000,000/wk.

KISMET | From EUR€ 3,000,000/wk

DREAM | From EUR€ 2,000,000/wk

92M FULLY CUSTOM SUPERYACHT | From US$ 1,500,000/wk

93M FULLY-CUSTOM SUPERYACHT | From EUR€ 1,470,000/wk

83m Limited Editions 272 Superyacht | From EUR€ 1,200,000/wk

95 meter CUSTOM | From EUR€ 1,200,000/wk

86M CUSTOM LUXURY YACHT | From EUR€ 1,200,000/wk

SAMSARA | From EUR€ 1,100,000/wk

ROMEA | From EUR€ 1,100,000/wk

80M MODERN CUSTOM YACHT | From EUR€ 1,085,000/wk

SOLANDGE | From EUR€ 1,000,000/wk

Caribbean Yacht News

33m luxury yacht FREEDOM for charter in ...

Last minute yacht charter deals in the ...

Benetti launches 34m motor yacht SIRENA ...

The caribbean yacht charter specials, special offer location: caribbean.

RESILIENCE | From US$ 487,500.00/wk

Sensational winter offer location: caribbean/bahamas.

TC | From US$ 149,900.00/wk

15% discount location: caribbean.

AMIGOS | From US$ 250,750.00/wk

20% discount location: caribbean.

EMERALD | From US$ 168,000.00/wk

Special discounted rate location: the bahamas / caribbean.

TOP FIVE II | From US$ 525,000.00/wk

Charter yacht disclaimer.

This document is not contractual. The yacht charters and their particulars displayed in the results above are displayed in good faith and whilst believed to be correct are not guaranteed. CharterWorld Limited does not warrant or assume any legal liability or responsibility for the accuracy, completeness, or usefulness of any information and/or images displayed. All information is subject to change without notice and is without warrantee. A professional CharterWorld yacht charter consultant will discuss each charter during your charter selection process. Starting prices are shown in a range of currencies for a one-week charter, unless otherwise marked. Exact pricing and other details will be confirmed on the particular charter contract. Just follow the "reserve this yacht charter" link for your chosen yacht charter or contact us and someone from the CharterWorld team will be in touch shortly.

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Sail the Caribbean

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Color and Contrast: the Complete Sailboat Vacation

Simply the perfect place to take a bareboat or skippered sailing holiday. Such a diverse collection of islands dotting the clear blue sea, each with its own unique appeal. Local cultures that fascinate and entertain, offering a welcome that keeps charterers returning to these waters year after year. With its 7,000 Islands and 28 Island nations, reliable trade winds and long sailing season, the Caribbean is a region that offers an endless amount of holiday enjoyment.

At Sail Connections, we work with all the best charter operators in the Caribbean, sorting through all the available boats and presenting all the best options to suit your vacation plans. Some of our operators offer extra services that are unique to their destinations. We personalize your proposal and give you the benefit of our knowledge and local contacts, to deliver a fabulous sailing holiday wherever there's a boat to charter in the Caribbean. 

Charter Sailing in the Caribbean

The Caribbean's numerous islands give you so many fabulous places to explore, so many diverse cultures to experience, that the permutations for planning a sailing charter are simply too numerous to list. The sailing distances between territories can be very short, and there are countless yacht charter bases scattered across the region. That opens the door to all manner of opportunities – from a seven-day sail around one distinct island nation to a multi-week one-way charter that takes in a wide variety of cultures and geographical features.

The Caribbean yacht charter season is busy from November through July. The peak season is mid-December to March, when winter escapees from North America and Europe arrive in their greatest numbers.

The hurricane season arrives late July and can last until early October, although storms here are rare and tend to deflect northwards towards the USA rather than hit the Caribbean. These months have their advantages in that they are the least costly for chartering, particularly in the British Virgin Islands. At that time of year it is in fact more likely to encounter light winds than it is storms.

As with many yacht charter locations, the shoulder season can be the best time to charter a yacht. In the Carribean that's from April to July. There are less shore-based visitors then, yet you can expect settled and sunny weather with warm, steady breezes prevailing.

We have access to over 30 charter bases in the region, from where you can take a sailboat vacation like no other. We select from the best boats available and guide you into the ideal sailing adventure that matches your interests and level of experience. The sailing options here are just about endless. Hopefully these pages will help you on your way to your much-anticipated Caribbean sailing holiday.

Regional Map of the Main Charter Sailing Areas

A One-way Cruise: Martinique to Grenada

There are quite simply countless itinerary options for sailing the caribbean. for many charterers a downwind cruise offers the crew conditions for maximum enjoyment. so here's a sample north to south course plan that gives you the prevailing breeze abaft. .

Waterfront at Fort de France, Martinique's largest town

Sailing from Martinique to Grenanda you can expect winds primarily from the northeast, especially around peak season either side of Christmas. Sailing this course involves short stretches of open water, with a stiff and steady breeze on your aft quarter. That makes for quick passages with most enjoyable sailing to a choice of Islands, whether it be for a lunch stop and a snorkel, or an overnight stay.

The eastern Caribbean islands that form a distinctive arc on the map are collectively the Lesser Antilles, a mixture of soverign states and territories governed by various powers. A trip along some of this chain exposes the voyager to a wide variety of cultures and customs in places that all sit in the idyllic picture-postcard surroundings of the movies and travel brochures. 

Starting in Martinique and sailing south, you are exploring the Windward Island group of the Antilles.

Wildlife viewing at its finest in the Tobago Cays

Like most of this group, Martinique was orginally colonised by France, and French flair is still in evidence there today. Martinique offers excellent on-shore facilities for the visitor, and is a popular base for boat charters. The island is mountainous, but with plenty of white sandy beaches to enjoy, especially in the south.

The next island is St Lucia. It's some 30 nautical miles to Rodney Bay on St Lucia's northwest, so to get there requires an early start. There are several top spots to visit down the island's sheltered western coast. Take time out to investigate Les Deux Pitons.

Another long but relaxing sail to St Vincent and the Grenadines, so-named because of their joint French and British colonial history. St Vincent has its Blue Lagoon that you'll probably overnight in, while the Grenadines island group, some of which confusingly belong to Grenada, provide numerous anchoring options.

Happy charterers enjoying their time ashore in the Grenadines

The Grenadines stretch all the way to Grenada, your final port of call, making this part of the voyage very convenient for a leisurely sail. Call in at one of the uninhabited Tobago cays for a real taste of desert island living, if only for a few hours.

Once offshore Carriacou you are in Grenadan territory. Grenada, like St Lucia & St Vincent and the Grenadines, is now an independent member of the British Commonwealth, but with historical French influence. This is the 'Island of Spice' where nutmeg and mace production are important to the economy. As is tourism, and there is plenty to entertain you before concluding your vacation and departing these fabulous sailing waters.

Once you have experienced all the pleasures of sailing the Caribbean, chances are you'll be back one day for more.

The Best Caribbean Charter Sailing Destinations

British Virgin Islands

US Virgin Islands

Puerto Rico & Spanish Virgin islands

Cayman Islands

St Martin, St Barts, Anguilla, St Kitts & Nevis

Antigua & Barbuda

Martinique, St Lucia & The Grenadines

Latest Blog Posts

Charter catamarans for modest sailing holiday budgets

Here we highlight some smaller catamarans finding favour with our charterers in the Mediterranean and elsewhere. Robert is our expert evaluator when it comes to helping you select the right boat for your sailing charter, and the following is his personal take on recent introductions to the charter boat market.

The popular Bali Catamaran in all its variations

The Bali catamaran, designed and built specifically with chartering in mind, has become so popular that it’s been hard to keep up with all the new models, hard to spot which one has just the right size and amenities to perfectly fit your group's sailing holiday charter needs. We can help you there.

The value of after-charter destination and boat reviews

At Sail Connections we offer a personal service based on long experience in the business and close attention to what's happening in the destinations we offer. We have also sailed a large number of those places, and can often speak from personal experience.  But we can't be everywhere.

Chartering in Turkiye: feedback we just have to share

Turkey is one of those charter destinations that doesn't fail to pleasantly surprise. We're always delighted when we receive such good reports as we did recently from a New Zealand client.

Barcelona gets ready for the America’s Cup

As well as the competition for the Auld Mug itself, the 37th America’s Cup in Barcelona will incorporate the first ever Women’s and Youth America’s Cup regattas. Chartering Barcelona 2024 will be in demand!

The Sail Connections Guarantee

One contact - every option - advice you can trust.

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• Personalising our proposal just for you
• Qualifying the operator as well as the boat
• Advising without bias based on 25+ years of experience
• We do more than just book yachts!

We will match any discount website offer on charter boat price, and still provide our customary high level of service.

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is jam-packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

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LUXURY YACHT CHARTERS & SAILING VACATIONS

All-Inclusive Yacht Charters

All-Inclusive Yacht Charters are with a captain and your own personal chef they tailor your charter for a needs and requests. allows you enjoy sailing in beautiful large vessels such as; Catamarans, Monohulls and Power Yachts designed for comfort.

Kayak, snorkel, sail, scuba dive, paddle-board, fish, island hop, or simply relax aboard a Caribbean yacht charter. We’ve listed just a few reasons below:

Fully Crewed, Catered & Private Sailing Yacht Charters Tailored for You & Your Guests

• Private Sailing Vacation
• Create Your Own Custom Itinerary
• Visit Untouched Islands
• Different Caribbean Destinations
• Unforgettable Memories
• Fully Prepared Meals by Your Own Private Chef
• Underwater Adventures with Sea Life

We Look Forward to Welcoming You Aboard!

Explore Destinations like the British Virgin Islands, St. John, Grenadines, Bahamas, and St. Marten!

All-Inclusive Yacht Charters are with a captain and your own personal chef they tailor your charter for a needs and requests. allows you enjoy sailing in beautiful large vessels such as; Catamarans, Monohulls and Power Yachts designed for comfort.  For more information, please visit our: Frequently Asked Questions.

Choose a vessel from our inventory:

FEATURED YACHT CHARTERS

• Sleeps 12 Guests
• 7 Kings, 1 Twin

• 157′ Mega Yacht
• 2 Kings, 2 Queens,
• 2 Doubles, 2 Twins, 2 pullman

• Sleeps 8 Guests
• 3 Queens, 1 Twin

BLUE HORIZON

• Sleeps 6 Guests
• 2 Kings, 1 Queen

POPULAR YACHT DESTINATIONS

Other Yacht Charter Destinations

• Florida Key’s
• St. Thomas, USVI
• British Virgin Islands

DAY CHARTER BOAT RENTALS

Scout in the Virgin Islands

Full-day charters 9:30 – 4:30 PM. US Virgin Islands or the British Virgin Islands $1800. Bar hop or visit exclusive beaches while you stop and snorkel along the way!

Our 38′ Scout comfortably holds 6+ passengers, allowing plenty of room to lay out on the sun deck or relax in the shade while enjoying a drink and listening to your favorite music.

1/2 Day or Full Day Charters

• Captain and Crew
• Complementary snorkel equipment and fins
• Coolers stocked with Ice, water and assorted beer.
• Abundance of cushioned seating and lounging areas in shade or sun.
• Dry storage for your personal items and gear.
• Full size restroom
• All required USCG approved safety equipment, and extra features not required by law.
• Food, Liquor, Fuel and Crew Gratuity is NOT included.

Fishing in the Virgin Islands

Everyday is a great day to book a fishing excursion. We can give you the fishing trip of a lifetime. Whether you are an experienced fisherman or just getting started the  mahi-mahi, tuna, wahoo, and big marlin await.

We have all the latest and best fishing gear, outriggers, navigation and sonar, along with some of the best and most experienced captains in the islands. Whether you choose a half day (3.5 hours) or a full day (7 hours) off shore trip, you’re guaranteed to have a good time.

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767  Crewed Luxury Yachts for Charter in the Caribbean

• Caribbean Yacht Charter

A Caribbean yachting vacation incorporates vast expanses of crystalline waters and endless clusters of idyllic paradisical islands, making for a picture-perfect family getaway. With its beautiful climate and spectacular coastlines that comprise iconic superyacht hotspots like the  Virgin Islands ,  St Barts  and  Antigua , a yacht rental in the Caribbean has an alluringly evergreen appeal.

Caribbean Yacht Booking Guide:

Caribbean Yacht Charters: At a Glance

Are the bahamas and the caribbean the same thing, popular destinations for yacht rentals in the caribbean, popular sub-regions in the caribbean, highlights of a caribbean yacht charter, who goes on a caribbean yacht charter, history and culture, types of yacht charters in the caribbean, how much does it cost to charter a yacht in the caribbean, when is the best time for caribbean yacht charters, where should i begin my caribbean yacht charter, popular marinas and moorings in the caribbean, how to book your yacht charter in the caribbean.

The Caribbean Sea comprises more than 7,000 islands, islets, reefs and cays, and is divided into three island arcs: that of the Greater Antilles in the north, the Lesser Antilles in the south, and the Leeward Antilles to the east.

• Ideal winter destination Boasting all-year-round pleasant weather, its powdery sand beaches and alluringly clear waters make it an especially popular choice for winter yacht charters.
• Easy-to-reach The Caribbean is well-connected to the US, with a high number of international airports flying directly into the region.
• Secluded anchorages With more than 7,000 islands and only a small percentage being inhabited, the world is your oyster when it comes to finding serenely beautiful anchorages.
• Snorkeling and diving paradise The Caribbean is home to some of the world's most impressive snorkeling and diving sites, meaning plenty of exciting underwater adventures where your eyes will be wide with wonder.
• Excellent superyacht marinas The Caribbean has numerous well-provisioned superyacht marinas to take your pick from, many of which have fantastic dining and shopping opportunities.

While the Bahamas is technically part of the Caribbean region, it is an island nation in its own right, forming part of the Lucayan Archipelago in the Atlantic. That said, the Caribbean is a vast area occupied by thousands of islands, coral reefs and islets, of which the Bahamas forms a part, along with strong political and cultural ties that have created a natural bond with its Caribbean neighbour. 

Practically speaking, however, if you are interested in cruising  the Bahamas  in conjunction with your Caribbean yacht charter, it is highly unlikely you'll be able to manage the distance during a typical 7-day charter, especially for itineraries that incorporate East Caribbean destinations such as Antigua and Saint Martin. You will need to decide which destination you prefer to spend your time in, or extend your charter vacation to incorporate both. 

To find out more about chartering in the region, check out our in-depth Bahamas destination guide for more information.

The most popular destinations for renting a yacht in the Caribbean are those located in the Lesser Antilles region, primarily the island groups of the Leeward Islands.  and the  Windward Islands .

For Leeward Island yacht rentals , Antigua, the Virgin Islands, St Martin, St Barts and St Kitts and Nevis garner the most attention, thanks to not only their splendid tropical landscapes but also their extremely well-provisioned superyacht marinas, fine dining options, impossibly hip bars and medley of designer boutiques bound to keep guests entertained from dawn till dusk.

Scattered like pearls along the aquamarine seas, you'll find sun-drenched Martinique, gorgeous Grenada and the ultra-secluded St Vincent and the Grenadines  are the top picks for slow-paced  Windward Island yacht charters .

Although not as popular, the islands that form the Greater Antilles , such as Jamaica, Cuba and Puerto Rico , are just as beautiful and offer an array of spectacular destinations to explore and discover on a luxury yacht charter.

Looking for the best superyacht hotspots in the Caribbean? These are the spellbinding locations guests find most enticing. If you are interested in any of these cruising grounds, we strongly advise booking as far in advance as possible.

• Antigua: the jet-set adore its unbelievable scenery, intriguing historical landmarks, lavish shopping options and a cluster of ivory-white sands coupled with gin-clear waters.
• St Martin/Sint Maarten : French and Dutch sides of the island combine to bring a fascinating fusion of influences, replete with outstanding diving spots and awe-inspiring topography. 
• St Lucia : considered the tropical jewel of the Windward Islands, it's virtually unspoiled. Bordered by lush rainforest and dark volcanic sands, it makes for a truly unique anchorage spot. 
• Grenada : known as the Isle of Spice thanks to being one of the world's largest exporters of mace and nutmeg, its capital St George is regularly called the Caribbean's most picture-perfect town. 
• St Barts : Well-known for its moniker "St Moritz of the Caribbean" due to its unique Swedish-French colonial heritage, this iconic tiny island is synonymous with glamour, movie stars and designer shopping. 
• St Croix, US Virgin Islands : The largest of the USVIs boasts a National Park, breath-taking scenic beauty and some of the best dive spots in the Caribbean.
• Puerto Rico : Affectionately known locally as the ‘island of enchantment’, Puerto Rico is a profusion of vibrant Latin culture entwined with the laid back rhythm of the Caribbean, with pristine beaches, excellent diving spots and exquisite local dishes.

A yacht rental vacation in the Caribbean delights guests with its truly endless number of things to see and do. Here are our top picks:

Don't Miss:

• Eden Rock St. Barts : one of the most in-demand hotels in the Caribbean, with a seven-star bar and spa.
• Hermitage Bay, Antigua : kick back and relax on this tropical beach that delivers on sensational views.
• Bagatelle, St. Barts : overlooking the glittering Gustavia harbor, this sophisticated bar and restaurant is a hugely popular superyacht spot, showcasing the finest of French-Caribbean cuisine.
• Basil's Bar, Mustique : legendary bar and restaurant designed by Philippe Starck, frequented by royals, supermodels and rockstars for decades.
• The Cotton House, Mustique : a wellness center unsurpassed in beauty.
• Watermelon Cay, St John, US Virgin Island s: dreamy islet surrounded by coral reefs and a veritable snorkeling wonderland
• Rhone Marine Park, British Virgin Islands : the wreck of the RMS Rhone is the BVIs' most popular dive site, and arguably one of the best in the Caribbean.
• Trunk Bay, St John, US Virgin Islands : all dazzling white sand lapped by the bluer-than-blue ocean, this island paradise ranks consistently among the world’s top 10 beaches.
• Jardines del Rey archipelago, Cuba : known locally as the ‘King’s Gardens’, this collection of islands is a registered UNESCO Biosphere Reserve and an island-hopper's paradise, offering myriad secluded beaches and sensational sunsets.

For anyone looking to get a dose of serious sunshine during the Northern Hemisphere winter, a yacht charter in the Caribbean is a seriously enticing prospect, with St Barts being the clear favorite for Christmas and New Year's Eve, thanks to the showstopping celebrations that take place in Gustavia Harbour.

For avid island hoppers, the Windward islands offer an enchanting itinerary full of sun-kissed isles and laid back charm juxtaposed with chic resorts and heavenly French-based cuisine, not to mention unrivalled vistas and sultry sunsets accompanied by warm rum-laced winds. 

Across all Caribbean destinations, keen divers and snorkelers will be in for a subaquatic treat, and you'll find a wide range of designer boutiques and ultra-high-end resorts peppered across the isles wherever you go.

The Caribbean is a mesmerizing melting pot of cultures and influences, rooted in its rich heritage and undeniably shaped by its history of colonization and waves of immigration. Each island group is highly diverse in terms of its language, music, customs, architecture and cuisine, but it's mainly English, Dutch, French or Spanish colonial influences that are keenly felt. While the mix of languages spoken will differ between island groups, English is widely spoken.

Caribbean cuisine sees influences from Africa, Europe, Latin America and Spain, Meat, seafood, coconut, potatoes, beans and tomatoes tend to feature heavily in local dishes.

Locals are friendly and regularly celebrate their culture, with music, food and wildly colorful festivals held throughout the year.

A luxury yacht rental vacation in the Caribbean is, without doubt, the most sublime way to experience this region, giving you exclusive access to heavenly anchorages that are otherwise impossible to reach or are far from the typical tourist trail.

Guests have boundless fleet options when it comes to a crewed Caribbean charter. If you don't know whether to go for a motor yacht, sailing yacht or catamaran to cruise Caribbean waters, we've laid out the main points worth considering.

Motor Yacht Charters in the Caribbean

A  luxury motor yacht charter  in the Caribbean is a seven-star way of uncovering the epic beauty of the Caribbean in total privacy. 

For regions with minimal water depth the ideal choice is a motor yacht with low draft, perfect for accessing shallow lagoons and secluded bays.

For those who have their heart set on a superyacht without a shallow draft, dropping anchor further out into deeper waters and then getting a tender ride ashore, so you can get up close and personal to exquisite island reefs and blue lagoons, is the preferred option.

Sailing Yacht Charters in the Caribbean

Chartering a sailing yacht in the Caribbean is ideal for guests looking for a slower pace to fully lap up the Caribbean rays with more outdoor deck space, and add a little old-school charm to their cruising adventure.

Even better, the majority of sailing charter yachts come equipped with a retractable keel, meaning reaching turquoise shallows is a breeze. But, if you are keen to charter a larger sailing yacht, keep in mind that some may still find their draft too deep for some areas, even with the keel up. 

Catamaran Charters in the Caribbean

Luxury catamaran charters are a firm guest favourite for those embarking on Caribbean vacation, especially in the Bahamas and the Virgin Islands. Thanks to their shallow draft, catamarans give you the ability to get close to cays and islets guests can savor the thrilling feeling of being able to jump off-board at almost any point. 

The charter cost of a motor yacht, sailing yacht or luxury catamaran rental in the Caribbean will vary according to the vessel's size, age, type, number of crew, as well as the location and duration of the vacation as well as the season it takes place. 

With so many options available, there’s something to suit every type of budget. For convenience we have listed the average prices for motor yacht and sailing yacht charters in the Caribbean below;

• For motor yacht rentals in the Caribbean, prices can range from $39,167 to $1.4m per week, plus expenses
• For luxury sailing yacht rentals in the Caribbean, prices can go from $29,855 to $276,495 weekly, plus expenses

The best time for luxury yacht charters in the Caribbean is between November and March, when guests can expect clement weather and vividly blue cloudless skies.

Another aspect to keep in mind is that this is also the time when you will have the largest selection of yachts to choose from, as most charter yachts descend on the Caribbean around November after the Mediterranean season has ended and any yacht maintenance has been carried out, before returning back to the Mediterranean in March/April.

The most popular starting point for a Caribbean yacht rental is usually in either Saint Martin/Sint Maarten or  Antigua,  both of which have international airports.

It is certainly possible to begin your charter in other Caribbean destinations, providing this has been agreed with the Owner and charter broker .

Where to End a Caribbean Yacht Charter

For most private Caribbean yacht charters, there isn't one definitive place where to disembark given the vastness of the region. However, what is likely is that you will finish your yacht rental vacation in the same location that you started. For example, the majority of  British Virgin Island yacht charters will begin and end in St Thomas, while for Antigua yacht charters , it'll be the iconic English Harbour.

sample itineraries

The Caribbean offers some of the most spellbinding berthing spots in the world. These tropical, barefoot hotspots are of the finest calibre, surrounded by jaw-dropping scenery, and often feature award-winning restaurants, hip boutiques, beach bars and more.

But which marinas are the best? Below are some charter favorites:

• Falmouth Harbour, Antigua: impressive marina facilities and scenery, catering to yachts up to 100m.
• Marina Fort Louis, Saint Martin: offers 150 berths for yachts up to 79m.
• Crown Bay in St Thomas (USVI): full-serviced marina with 99 slips, including 16 berths for superyachts up to 60m
• Port Louis Marina, Grenada: idyllically located, with 227 moorings for yachts up to 91m.
• Port de Gustavia, Saint Barts: widely regarded as one of the most beautiful natural harbours in the world, accommodating up to 152 yachts up to 152m.
• Puerto Del Rey, Puerto Rico : conveniently located as a jumping off point for yacht charters incorporating the Virgin Islands and Lesser Antilles, this marina has plentiful wet slips, including capacity for yachts up to 200ft (60m) LOA.

We strongly advise booking through a qualified  yacht charter broker at least three months in advance for all Caribbean yacht charters. By doing so, you will increase the likelihood of securing your preferred dates and you will have a greater selection of yachts on offer to choose from.

This also ensures your yacht broker has enough time to craft a carefully curated itinerary and secure an overnight berth in the most popular Caribbean marinas.

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The caribbean yacht charter itineraries.

Make every moment count during your superyacht vacation with our carefully curated yacht charter itineraries, tailored so you can experience the very best of the paradisiacal islands of the Caribbean and ensure your yacht charter is a truly memorable one. Designed by yachting experts, we've cultivated itineraries that will satisfy a range of requirements.

For yacht charter guests seeking a little glitz and glamour on their vacation, a 7-day charter around the Leeward Islands is a must, comprising Caribbean gems such as Saint Barthelemy, renowned for its A-list celebrity culture and designer shopping, as well as the perennial favourite Antigua. For sheer unadulterated bliss, incorporate the Virgin Islands on a 14-day yacht charter, promising idyllic stretches of pristine sands lapped by waters in every shade of blue.

Discover the Caribbean

Winter Getaways, Tropical Paradise Islands, Snorkeling & Scuba Diving, Crystal Clear Waters, Beautiful Secluded Anchorages, Well-Provisioned Superyacht Marinas

When to Go:

December - March

International Airports:

• Princess Juliana Airport (St. Maarten)
• V.C. Bird Airport (St. John's, Antigua)
• Luis Muñoz Marín Airport (Carolina, Puerto Rico)
• Grantley Adams Airport (Bridgetown, Barbados)
• Lynden Pindling Airport (Nassau, The Bahamas)

Luxury Yachts for Charter in the Caribbean 2024 & 2025

Crewed charter yachts in the caribbean.

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92m   Neorion

from $1,075,000 p/week ♦︎

115m Lurssen

115m   2021

from $2,823,000 p/w eek ♦︎

Black Pearl 14

105m Oceanco

105m   2018

Christina O 34

99m Canadian Vickers

99m   1943/2020

from $760,000 p/w eek ♦︎

Carinthia VII 12

97m Lurssen

97m   2002/2023

from $1,520,000 p/w eek ♦︎

97m Feadship

97m   2017/2022

from $1,737,000 p/w eek ♦︎

Madsummer 12

95m Lurssen

from $1,303,000 p/w eek ♦︎

93m Feadship

Aquarius 12

92m Feadship

from $1,500,000 p/w eek

Queen Miri 36

92m Neorion

92m   2004/2023

from $1,075,000 p/w eek ♦︎

Lady Lara 12

91m Lurssen

91m   2015/2023

from $1,400,000 p/w eek

90m Corsair Yachts

90m   2007/2021

from $497,000 p/w eek

90m Oceanco

89m Oceanco

from $1,100,000 p/w eek

89m   2015/2023

Maltese Falcon 12

88m Perini Navi

88m   2006/2023

from $490,000 p/w eek

86m Scheepswerf Gebr. van der Werf

86m   1998/2024

from $537,000 p/w eek ♦︎

Man of Steel 12

86m Oceanco

86m   2010/2023

from $1,000,000 p/w eek

O'Ptasia 12

85m Golden Yachts

85m   2018/2022

from $977,000 p/w eek ♦︎

Victorious 12

85m Ak Yachts

from $868,000 p/w eek ♦︎

Le Ponant 32

84m   1990/2022

from $494,000 p/w eek ♦︎

Savannah 12

84m Feadship

84m   2015/2020

from $1,085,000 p/w eek ♦︎

Alfa Nero 12

81m Oceanco

81m   2007/2021

from $728,000 p/w eek *

Sea Eagle 11

81m Royal Huisman

81m   2020/2022

from $597,000 p/w eek ♦︎

Elements 12

80m Yachtley

Excellence 12

80m Abeking & Rasmussen

from $1,150,000 p/w eek

Amaryllis 12

78m Abeking & Rasmussen

78m   2011/2022

from $770,000 p/w eek

78m Golden Yachts

78m   2023/2024

from $814,000 p/w eek ♦︎

from $480,000 p/w eek

Stad Amsterdam 28

76m Damen Oranjewerf

76m   2000/2009

from $102,500 p/w eek

Huntress 12

76m Lurssen

from $725,000 p/w eek

75m Admiral Yachts

75m Feadship

from $900,000 p/w eek *

75m Abeking & Rasmussen

from $880,000 p/w eek

from $988,000 p/w eek ♦︎

74m Nobiskrug

74m   2008/2013

from $564,000 p/w eek ♦︎

73m Delta Marine

73m   2006/2015

from $525,000 p/w eek

Nautilus 12

73m Picchiotti

from $813,000 p/w eek ♦︎

73m Lurssen

73m   2006/2020

from $615,000 p/w eek

Quantum of Solace 12

73m Turquoise Yachts

73m   2012/2022

from $574,000 p/w eek

Game Changer 17

72m Damen Yachting

72m   2017/2020

from $450,000 p/w eek

72m   2010/2023

from $600,000 p/w eek

72m Dunya Yachts

72m   2013/2020

from $660,000 p/w eek

Talisman C 12

71m Turquoise Yachts

71m   2011/2020

from $567,000 p/w eek

70m Feadship

from $650,000 p/w eek

Sherakhan 26

70m Vuijk Scheepswerven

70m   2005/2022

from $592,000 p/w eek ♦︎

Sycara V 12

68m Nobiskrug

68m   2010/2017

Wayfinder 12

68m Astilleros Armon

from $375,000 p/w eek

67m Icon Yachts

67m   2010/2020

from $540,000 p/w eek

67m Alloy Yachts

67m   2011/2019

from $353,000 p/w eek ♦︎

67m Benetti

from $680,000 p/w eek

67m Shadow Marine

67m   2007/2008

from $120,000 p/w eek

66m   2014/2023

66m Rossinavi

from $637,000 p/w eek *

Invictus 12

66m Delta Marine

66m   2013/2020

from $650,000 p/w eek *

65m Benetti

Ventum Maris 12

66m   2011/2021

from $530,000 p/w eek

Eternity 17 7 12

65m Codecasa

65m   2010/2022

from $390,000 p/w eek

Illusion 12

65m   2013/2019

from $462,000 p/w eek

Resilience 12

Silver Angel 12

65m   2009/2015

from $425,000 p/w eek

64m Benetti

64m   2016/2021

from $475,000 p/w eek

63m Halter Marine

63m   1978/2022

from $350,000 p/w eek *

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Crewed Luxury Yachts in the Caribbean

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Caribbean Yacht Charter Q&A

The best time to visit the Caribbean is generally December to April, when it's a little cooler and less humid. But the best month to visit can differ depending on the island, budget and interests you have. For example, some yacht charter guests may decide to visit May to June and late November, when weather is still fantastic but there are fewer crowds.

We advise booking your Caribbean yacht rental at least three months in advance to ensure you get the yacht you desire. The longer you leave it, the fewer choices you will have to rent in the Caribbean.

For your Caribbean superyacht charter, you will need to provide a completed charter agreement and 50% of the charter fee as a deposit. This is payable once the contract has been signed.

When booking a Caribbean yacht rental, do keep in mind the costs that aren't included in the base rate, namely VAT and the APA (Advance Provisioning Allowance). The APA is usually paid in advance of the charter and is commonly set at 30% of the charter fee. This allowance covers expenses such as fuel, berthing, food and drinks, as well as any special requests. 

Please consult your yacht charter broker for any other costs you may need to factor in for your yacht charter in the Caribbean.

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Sail away to white sand beaches, consistent Caribbean trade winds, clear blue water, sheltered island bays great for cruising, world-class dive sites, award winning yachts and crew, and sunshine every day of the year.

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These crewed catamaran charter specials are available for new reservations sailing from St Thomas or Tortola in the Virgin Islands, or elsewhere in the Caribbean. Contact us now for further information and a no-obligation quote.

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Our customers say it best. Check out their feedback.

The crew was wonderful. Kayla and Chris fit in with our family perfectly and made us feel comfortable and at home aboard Felix. Their humor and knowledge were both greatly appreciated!

The food was fantastic; Chris truly spoiled us! I personally have a challenging diet with several allergies and he made sure every meal felt complete vs feeling like an “allergy friendly” meal. And it was all delicious!

The yacht was very comfortable and clean. It had all of the accommodations we needed - nothing was missing... I enjoyed the various different viewpoints to sit or lounge at while we went from island to island.

Kress S, aboard Catamaran Felix , November 2023  sailing the Virgin Islands

Melody D, aboard Catamaran Excess , January 2023  sailing the British Virgin Islands

Mathieu C, aboard Catamaran Cashmere , December 2022  sailing the Caribbean Leeward Islands

> See all of our crewed yacht charter reviews

Caribbean Yacht Charter Vacations

A crewed Caribbean yacht charter offers you the freedom to explore this tropical paradise without limits and at your own pace.

With accommodation, a professional captain, a personal chef, all meals, cocktails, wine, beer, snacks, fuel, equipment, and water toys included, few other vacations offer such an extraordinary experience and value.

Itineraries are completely flexible within your cruising area. Sail the diverse US and British Virgin Islands, the undeveloped and resort islands of the Caribbean Grenadines, or charter a luxury power yacht to cruise St. Martin, St. Barts, and Antigua in the Caribbean Leeward Islands.

Sailing Direction's charter brokers help you book a private crewed yacht in the Caribbean for any group size and budget. Whether you're looking for a family sailing vacation, a couple's adventure holiday, a BVI yacht charter, or a honeymoon or anniversary celebration - we've got you covered for an unforgettable crewed yacht charter experience.

St. Vincent & The Grenadines Bareboat Charter Fleet

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NEW Yachts!

We are partnering with American and international yacht sales companies.

Neptune Fleet

Discover the epitome of seafaring indulgence with Barefoot Yachts’ Neptune fleet, meticulously outfitted and maintained for discerning adventurers. Our luxury comfort yachts redefine relaxation, boasting opulent amenities and spacious layouts, ensuring an unrivaled at-anchor experience. Immerse yourself in tranquility and luxury as you cruise the pristine waters of the Grenadines. On the other hand, our luxury performance fleet stands as a testament to superior sailing, designed to thrill and delight enthusiasts seeking exhilarating voyages. Sail with precision, power, and grace, embracing the wind and waves like never before, reveling in the exciting sailing conditions for which the Grenadines are famous. Barefoot Yachts, a boutique family-owned charter company, invites you to savor the finest in nautical luxury.

Viewfinder 2020 Bali 4.1

Ulysses Lagoon 42

Sonhos Bali 4.4

Sonder Seawind 1260

Hearts Desire Lagoon 46

Catara NEEL 43

AONYX O-Yacht 45

Navigator fleet.

Embark on a cost-effective voyage without compromising luxury aboard Barefoot Yachts’ Navigator fleet, featuring 5-year-old and older sailing yachts. Choose from our distinct categories: luxury comfort yachts, tailored for an idyllic at-anchor escape with opulent amenities, or luxury performance yachts, finely tuned to deliver thrilling and memorable sailing journeys. Experience the blend of affordability and elegance as you navigate the beautiful waters, soaking in the sunsets and salty breeze. Barefoot Yachts, a cherished boutique family-owned charter company, invites you to relish an unmatched balance of economy and indulgence on the high seas.

Betty Blue Beneteau 50

Inordinate Venezia 42

Lady Di Oceanis 41

Pelican Pete Sun Odyssey 34

Willow Dew Lagoon 39

Fully crewed yachts.

Experience unparalleled opulence aboard A Barefoot Yachts’ fully crewed private luxury yacht charter, where desires are effortlessly met by an attentive crew dedicated to pampering guests with first-class service. Indulge in delectable gourmet meals prepared by your private chef and revel in the freedom to sail on your schedule. With over 32 years of navigating the Grenadines, Barefoot Yachts offers a unique understanding of the region, ensuring an exclusive journey through these breathtaking waters, enriched by their expert insight into the cruising grounds and the vibrant local culture.

Splendido Beneteau 57

Rob Roy CATANA 531

Racing fleet.

Embark on a sailing adventure of a lifetime with Barefoot Yachts’ race charters in the Caribbean! Picture yourself on the tiller of a professionally maintained, high-performance sailboat, cutting through the azure waters of the Caribbean. Experience the exhilaration of competitive racing and join the ranks of international sailors, embracing the thrill of challenging race courses set amidst the incredible beautiful of these iconic islands. Revel in post-race festivities under starlit Caribbean skies, sipping fine local rums and dancing to the rhythm of this vibrant paradise. Unleash your inner competitive sailor and experience some of the best grand prix racing events in the world, with Barefoot Yachts.

SALT FISH J 24

HAPPY Melges 20

SMILE (#212) Melges 20

GONE C&C 30

SEAPLANE Melges 32

Navigator and neptune fleet prices.

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Caribbean Sailboat Charter: An Unforgettable Adventure

The Caribbean is one of the most beautiful and sought-after destinations for sailing enthusiasts. With its turquoise waters, white sandy beaches, and vibrant culture, it’s no wonder why so many people flock to this region every year. Caribbean sailboat charter can be an unforgettable experience, but there are many things to consider before embarking on your journey.

In this article, we will provide an overview of the coastline and popular charter areas in the Caribbean, discuss nautical infrastructure and sailing conditions, and explore the nature, history, and cuisine of the region. We will also touch on the costs associated with marinas, anchorages, and moorings, as well as activities available outside of sailing. Finally, we will weigh the pros and cons of chartering in the Caribbean compared to other popular sailing destinations. So, sit back, relax, and let’s dive into the world of chartering a sailboat in the Caribbean!

If you are interested in other destinations, check out my  Top 10 Sailboat Charter Destinations

Overview of the Coastline

The Caribbean boasts some of the most breathtaking coastlines in the world, with crystal-clear waters and pristine beaches that attract visitors from all over the globe. The region encompasses a vast area, spanning from the Bahamas in the north to Trinidad and Tobago in the south, and encompassing more than 7,000 individual islands.

One of the most striking features of the Caribbean coastline is its diversity. Each island and region has its unique character, from the rugged and dramatic cliffs of the Virgin Islands to the gently curving bays of the Bahamas. Some areas are characterized by towering cliffs and rocky outcroppings, while others feature long stretches of powdery white sand beaches fringed with coconut palms.

The Caribbean also boasts a wealth of stunning coral reefs, which attract divers and snorkelers from around the world. The coral formations are home to a vast array of marine life, including colorful fish, sea turtles, and even sharks.

Perhaps the most iconic feature of the Caribbean coastline is its turquoise waters, which are warm and inviting year-round. The colors of the water can vary depending on the depth, with shallower areas appearing a bright turquoise and deeper areas taking on a deeper blue-green hue.

One of the best ways to experience the beauty of the Caribbean coastline is by sailboat. With a sailboat, you can explore secluded coves and bays that are inaccessible by land, and enjoy the freedom to chart your course and discover hidden gems at your own pace.

Whether you are seeking adventure or relaxation, the Caribbean coastline has something to offer everyone. From the bustling beaches of Jamaica to the tranquil bays of the Grenadines, there is no shortage of beauty and wonder to be found in this stunning region of the world.

Charter Areas in the Caribbean

The Caribbean is home to a diverse array of charter areas, each offering its unique blend of natural beauty, cultural richness, and recreational opportunities. Here are some of the most popular charter areas in the Caribbean:

British Virgin Islands

The British Virgin Islands, also known as the BVI, is a sailing mecca, offering some of the most protected waters in the Caribbean. The BVI is made up of more than 60 islands and cays, each with its unique character and attractions. The islands are renowned for their stunning scenery, crystal-clear waters, and consistent trade winds, making them an ideal destination for sailors of all skill levels.

St. Martin/St. Maarten

This island is divided into two halves, with the French side to the north and the Dutch side to the south. St. Martin/St. Maarten offers a unique blend of European and Caribbean culture, with a diverse array of restaurants, bars, and shops. The island’s natural beauty includes pristine beaches, lush tropical forests, and scenic coves and bays.

Antigua is one of the most popular charter areas in the Caribbean, known for its idyllic white sandy beaches, calm waters, and year-round sunshine. The island boasts numerous protected bays and harbors, making it an ideal location for sailing. Antigua is also home to a diverse array of cultural and historical attractions, including Nelson’s Dockyard National Park, a UNESCO World Heritage site.

Grenada, also known as the “Spice Isle,” is famous for its fragrant nutmeg and other spices. The island’s coastline is dotted with secluded bays and coves, making it an excellent destination for exploring by sailboat. Grenada’s vibrant culture includes a lively music and dance scene, as well as a wealth of historical and cultural sites.

St. Lucia is one of the most picturesque islands in the Caribbean, with towering mountains, lush rainforests, and stunning beaches. The island’s coastline features numerous protected bays and harbors, making it an ideal location for sailing. St. Lucia is also home to a wealth of cultural and historical attractions, including the UNESCO World Heritage site of the Pitons.

The Bahamas are a collection of more than 700 islands and cays, each with its unique character and attractions. The islands are renowned for their pristine beaches, turquoise waters, and excellent fishing and diving opportunities. The Bahamas offer a wealth of cultural and historical attractions, including the vibrant Junkanoo festival and the colonial architecture of Nassau.

Cuba is a unique charter destination, offering a fascinating blend of history, culture, and natural beauty. The island’s coastline features numerous protected bays and harbors, as well as a wealth of cultural and historical sites. Cuba’s vibrant culture includes music, dance, art, and cuisine, making it an excellent destination for those seeking a truly immersive cultural experience.

These are just a few of the many charter areas in the Caribbean, each offering its unique blend of natural beauty, cultural richness, and recreational opportunities. Whether you are seeking adventure, relaxation, or cultural immersion, the Caribbean has something to offer everyone.

Popular Routes

Sailing in the Caribbean offers endless possibilities for exploring stunning natural beauty and vibrant culture. Here are some popular routes to sail in the following charter areas:

Route 1: Start from the marina in Tortola and sail to Norman Island, famous for its snorkeling and diving spots. Then head to Cooper Island, which is known for its white sandy beaches and excellent restaurants. The next stop is Virgin Gorda, home to The Baths, a unique geological formation of granite boulders. Finish the route by sailing back to Tortola.

Route 2: Start from the marina in Tortola and sail to Jost Van Dyke, which is known for its lively beach bars and stunning scenery. Then head to Anegada, the only coral island in the BVI and a popular spot for snorkeling and diving. Finish the route by sailing back to Tortola.

Route 1: Start from the marina in St. Martin and sail to Anguilla, which is renowned for its pristine beaches and crystal-clear waters. Then head to St. Barts, which is famous for its chic boutiques, gourmet restaurants, and stunning beaches. Finish the route by sailing back to St. Martin.

Route 2: Start from the marina in St. Martin and sail to Saba, a volcanic island known for its stunning scenery and excellent diving opportunities. Then head to St. Kitts and Nevis, home to lush rainforests, historic sites, and beautiful beaches. Finish the route by sailing back to St. Martin.

Route 1: Start from the marina in Jolly Harbour and sail to Barbuda, which is renowned for its pink sandy beaches and abundant wildlife. Then head to Green Island, a pristine uninhabited island with excellent snorkeling and diving spots. Finish the route by sailing back to Jolly Harbour.

Route 2: Start from the marina in English Harbour and sail to Guadeloupe, a French island with a wealth of cultural and historical attractions. Then head to the islands of Dominica and Martinique, which are famous for their lush rainforests, scenic waterfalls, and vibrant culture. Finish the route by sailing back to English Harbour.

Route 1: Start from the marina in St. George’s and sail to Carriacou, a small island known for its excellent diving and snorkeling opportunities. Then head to the Tobago Cays, a group of uninhabited islands with crystal-clear waters and abundant marine life. Finish the route by sailing back to St. George’s.

Route 2: Start from the marina in St. George’s and sail to Union Island, which is known for its stunning scenery and vibrant culture. Then head to Bequia, a charming island with a relaxed atmosphere and excellent restaurants. Finish the route by sailing back to St. George’s.

Route 1: Start from the marina in Rodney Bay and sail to Soufriere, home to the famous Pitons, a UNESCO World Heritage site. Then head to Marigot Bay, a picturesque cove with excellent dining and shopping options. Finish the route by sailing back to Rodney Bay.

Route 2: Start from the marina in Rodney Bay and sail to the island of Martinique, which is famous for its vibrant culture and lush rainforests. Then head to St. Vincent and the Grenadines, home to stunning beaches, excellent diving and snorkeling spots, and charming local villages. Finish the route by sailing back to Rodney Bay.

Route 1: Start from the marina in Nassau and sail to the Exuma Cays, a chain of islands and cays known for their turquoise waters, white sand beaches, and abundant wildlife. Explore landmarks such as Thunderball Grotto, a natural cave featured in the James Bond movie “Thunderball.” Finish the route by sailing back to Nassau.

Route 2: Start from the marina in Marsh Harbour and sail to Elbow Cay, one of the Abacos’ most picturesque cays with a charming colonial-era village. Then head to Great Guana Cay, home to one of the Bahamas’ most beautiful beaches. Finish the route by sailing back to Marsh Harbour.

Route 1: Start from the marina in Havana and sail to Cayo Levisa, a small island with pristine beaches and excellent snorkeling opportunities. Then head to the Isle of Youth, home to lush forests, pristine beaches, and numerous shipwrecks for scuba diving. Finish the route by sailing back to Havana.

Route 2: Start from the marina in Cienfuegos and sail to Trinidad, a historic city known for its colorful architecture and lively music scene. Then head to Cayo Largo del Sur, a small island with stunning beaches and crystal-clear waters. Finish the route by sailing back to Cienfuegos.

These popular routes offer a mix of natural beauty, cultural experiences, and exciting activities that make sailing in the Caribbean a unique and unforgettable adventure. Keep in mind that weather conditions and other factors may affect the feasibility of these routes, so it’s important to consult with local authorities and plan your trip accordingly.

Nautical Infrastructure

When it comes to nautical infrastructure, the Caribbean offers a range of options for sailors, from modern marinas to rustic anchorages. However, there are some differences between the infrastructure in the Caribbean and other countries that are worth noting.

One of the most noticeable differences is the variety of options available in the Caribbean. Unlike some other sailing destinations, such as the Mediterranean, where marinas are the primary option for mooring, the Caribbean offers a range of choices, from marinas to anchorages, moorings, and even offshore islands. This gives sailors the flexibility to choose the type of infrastructure that best fits their needs and preferences.

Another difference is the cost of nautical infrastructure. While some marinas in the Caribbean can be quite expensive, especially during peak season, there are also many more affordable options, such as anchorages and moorings, that allow sailors to enjoy the region’s beauty without breaking the bank.

In terms of nautical services, the Caribbean offers a range of options as well, from full-service marinas with amenities such as fuel docks, restaurants, and showers, to smaller marinas and anchorages that offer more basic services. Additionally, there are many yacht provisioning companies and chandleries throughout the region that cater to sailors’ needs, from stocking up on food and supplies to repairing or upgrading their vessels.

One thing that stands out in the Caribbean’s nautical infrastructure is the importance of environmental sustainability. With the region’s stunning natural beauty and fragile ecosystems, many marinas and sailing companies have taken steps to reduce their environmental impact, such as implementing recycling programs, reducing energy consumption, and promoting sustainable tourism practices.

While there may be some differences in nautical infrastructure between the Caribbean and other sailing destinations, the region offers a wide range of options and services that cater to sailors’ needs and preferences, as well as a commitment to preserving the region’s natural beauty for generations to come.

Sailing Conditions

Sailing conditions in the Caribbean can vary depending on the time of year, location, and weather patterns. However, in general, the region is known for its favorable sailing conditions, with calm seas, steady trade winds, and warm temperatures that make for an enjoyable and comfortable sailing experience.

The trade winds are one of the most significant factors affecting sailing conditions in the Caribbean. These prevailing winds blow from the east-northeast and are relatively consistent throughout the year, with speeds typically ranging from 10-20 knots. This makes for ideal sailing conditions, as sailors can rely on the wind to propel their vessels and maintain a steady course.

While the trade winds are generally reliable, there are some variations depending on the time of year. During the summer months, the winds may be slightly weaker, and there is a greater chance of rain and thunderstorms. In contrast, during the winter months, the winds may be stronger, with higher speeds and gusts, and the weather tends to be drier and more stable.

Another factor affecting sailing conditions in the Caribbean is the sea state. While the waters are generally calm and protected, there can be some variations depending on the location and weather conditions. In some areas, such as the Windward Islands, the seas can be choppy due to the prevailing winds and currents. In other areas, such as the Bahamas, the waters are shallow and can be affected by tidal changes and sandbars.

It’s also worth noting that the Caribbean is located in the hurricane belt, and there is a risk of tropical storms and hurricanes during the hurricane season, which runs from June through November. While these weather events are relatively rare, they can pose a significant threat to sailors, and it’s important to monitor weather forecasts and take appropriate precautions when sailing in the region.

Sailing conditions in the Caribbean are generally favorable, with steady trade winds, calm seas, and warm temperatures that make for an enjoyable and comfortable sailing experience. However, it’s important to be aware of the variations in weather and sea state and take appropriate precautions to ensure a safe and enjoyable trip.

Best time to charter

Chartering a sailboat in the Caribbean is a dream for many people. But when is the best time to do it? There are different factors to consider, such as weather conditions, crowds, and costs. Here’s a breakdown of the best times to charter a sailboat in the Caribbean:

High Season (December – April)

The high season in the Caribbean runs from December through April, and it’s considered the best time to charter a sailboat in terms of weather conditions. The weather is typically dry, with plenty of sunshine and comfortable temperatures ranging from the mid-20s to mid-30s Celsius. The trade winds are also consistent, making for ideal sailing conditions.

However, because this is the peak tourist season, the marinas and anchorages can be crowded, and the costs for chartering a sailboat may be higher. You’ll need to book your charter well in advance to secure your preferred dates and locations.

Shoulder Season (May – June, November)

The shoulder season in the Caribbean runs from May through June and November, and it offers a good compromise between favorable weather conditions and lower costs. During this time, the crowds are thinner, and the marinas and anchorages are less crowded. The temperatures are also still warm, with average highs ranging from the mid-20s to low-30s Celsius.

However, there is a greater chance of rain and thunderstorms during the shoulder season, particularly in November, when hurricane season is still in effect. If you plan to charter a sailboat during the shoulder season, it’s important to keep an eye on weather forecasts and take appropriate precautions to ensure a safe trip.

Low Season (July – October)

The low season in the Caribbean runs from July through October, and it’s the least crowded and most affordable time to charter a sailboat. However, this is also the time when the weather is the most unpredictable, with a higher chance of rain, thunderstorms, and tropical storms or hurricanes.

If you plan to charter a sailboat during the low season, it’s essential to keep an eye on weather forecasts and take appropriate precautions to ensure a safe trip. However, the low season can also offer some advantages, such as lower charter prices and more availability.

The best time to charter a sailboat in the Caribbean depends on your preferences and priorities. If you prioritize ideal weather conditions and don’t mind the crowds and higher prices, the high season is the best option. If you want to save money and avoid crowds, the low season may be a good choice, but you’ll need to be prepared for the possibility of unpredictable weather. The shoulder season offers a good balance between favorable weather and lower costs, but again, be aware of the higher chance of rain and thunderstorms.

Boat Types to Charter

When it comes to chartering a sailboat in the Caribbean, choosing the right boat type can make all the difference in your sailing experience. Here are some factors to consider when selecting a boat type for your Caribbean sailing adventure:

Monohulls are a popular option for chartering in the Caribbean due to their authentic sailing experience. They are a great option for experienced sailors who want a challenging and exciting sailing experience. Monohulls perform well in strong winds and are suitable for longer trips or offshore sailing. However, they may not provide as much space or comfort as other boat types.

Catamarans are another popular option for chartering in the Caribbean. They feature two hulls connected by a deck and offer more living space, storage, and outdoor areas than monohulls. Catamarans are stable and provide a comfortable and spacious sailing experience, making them an excellent option for families, couples, and groups of friends. They are also ideal for anchoring in shallower waters closer to shore, allowing for more exploration of the Caribbean’s beautiful islands. Additionally, catamarans can be great for privacy as they have separate hulls for sleeping areas.

Motor Yachts

Motor yachts provide the ultimate luxury and convenience for chartering in the Caribbean. They have powerful engines, allowing them to travel at higher speeds and cover longer distances in a shorter amount of time. Motor yachts also offer a wide range of amenities, such as air conditioning, entertainment systems, and spacious cabins. They are ideal for those who want to explore the Caribbean in style and comfort and can be great for anchoring in secluded areas for privacy.

Trimarans are similar to catamarans, with three hulls instead of two. They offer the stability of a catamaran while providing speed and performance like a monohull. Trimarans have a shallow draft, allowing them to navigate shallow waters and explore secluded areas of the Caribbean. They are a great option for experienced sailors looking for a high-performance sailing experience.

Gulets are traditional wooden sailboats that originated in Turkey. They are popular for chartering in the Caribbean due to their unique appearance and charm. Gulets typically have multiple cabins and outdoor spaces, making them ideal for larger groups or families. They provide a comfortable and laid-back atmosphere, providing a relaxed sailing experience. Gulets can be a great option for privacy as well since they offer multiple cabin spaces.

No matter which boat type you choose, chartering a sailboat in the Caribbean offers a unique and unforgettable experience. You can anchor in secluded coves and bays, swim off the boat in crystal clear waters, and explore the islands at your own pace. The Caribbean is known for its warm weather, calm seas, and trade winds, making it a perfect destination for sailing. You can sail to different islands and experience their unique cultures, cuisines, and history.

When selecting a boat type, consider what is important to you for your sailing experiences, such as space, comfort, performance, privacy, and amenities. With a variety of boat types to choose from, you can find the perfect one for your Caribbean sailing adventure.

Nature, History, and Culture

The Caribbean is a region rich in history, culture, and natural beauty, making it an ideal destination for a sailing vacation. In this chapter, we will explore some of the top attractions to see during a sailing vacation in the Caribbean, including its unique culture, stunning landscapes, and fascinating history.

Historical Sites

The Caribbean is home to several significant historical sites, including colonial forts and sugar plantations, that offer a glimpse into the region’s rich history. Examples of such sites include the 17th-century Fort Charles in Jamaica, the 16th-century Fort San Cristobal in Puerto Rico, and the historic Brimstone Hill Fortress in St. Kitts and Nevis.

Natural Wonders

The Caribbean is home to a vast array of natural wonders, from lush rainforests and stunning waterfalls to coral reefs and marine life. During a sailing vacation in the Caribbean, visitors can explore these natural wonders, including the Virgin Islands National Park in St. John, the Pitons in St. Lucia, and the famous Baths in the British Virgin Islands.

National Parks and Protected Areas

The Caribbean has several protected areas and national parks, including the Morne Trois Pitons National Park in Dominica, the Buccoo Reef Marine Park in Tobago, and the Christoffel National Park in Curacao. These parks offer stunning natural landscapes and unique wildlife, with opportunities for hiking, birdwatching, and diving.

Beaches and Coral Reefs

The Caribbean is renowned for its beautiful beaches and crystal-clear waters. From the pink sands of Harbour Island in the Bahamas to the secluded coves of Tobago Cays in St. Vincent and the Grenadines, the region’s beaches are a true paradise for beach lovers. The Caribbean is also home to some of the world’s most spectacular coral reefs, providing excellent opportunities for snorkeling and diving.

Caribbean Culture

The Caribbean is known for its vibrant and diverse culture, which is showcased in its music, art, cuisine, and festivals. Visitors to the Caribbean can experience traditional music such as reggae, calypso, and soca, and participate in colorful festivals like Carnival in Trinidad and Tobago or Junkanoo in the Bahamas. The region’s unique blend of African, European, and indigenous cultures has resulted in a rich and dynamic cultural tapestry.

Caribbean Cuisine

The Caribbean is a melting pot of cultures, and its cuisine is a reflection of that diversity. The region’s food is influenced by African, European, and indigenous traditions, resulting in a vibrant and flavorful culinary scene. In this chapter, we will explore some of the signature dishes and ingredients of the Caribbean.

One of the most iconic dishes of the Caribbean is jerk chicken. Originating in Jamaica, jerk chicken is a spicy dish that is marinated in a mixture of herbs and spices, including allspice, thyme, and Scotch bonnet peppers. It is typically cooked on a grill or over an open flame, giving it a smoky flavor.

Another popular dish in the Caribbean is conch fritters. Conch is a type of mollusk that is found in the waters of the Caribbean, and it is a staple in many island cuisines. Conch fritters are made by mixing chopped conch with flour, spices, and vegetables, and then deep-frying the mixture into bite-sized pieces.

Seafood is a major component of Caribbean cuisine, and many islands boast an abundance of fresh fish, lobster, and shrimp. One popular seafood dish is grilled fish, which is often marinated in citrus juice and herbs and then grilled to perfection. Lobster is also a popular seafood option in the Caribbean, and it is often served with garlic butter or a spicy sauce.

Plantains are another staple ingredient in Caribbean cuisine. Similar to bananas, plantains are larger and firmer and are used in a variety of dishes. One popular preparation is tostones, which are made by slicing green plantains and then frying them until crispy. They are often served as a side dish or as a snack.

Finally, no discussion of Caribbean cuisine would be complete without mentioning rum. The Caribbean is home to some of the world’s finest rum distilleries, and the spirit is a key ingredient in many island cocktails, including the famous piña colada and the daiquiri.

Costs of Marinas, Anchorages, and Moorings

Chartering a sailboat in the Caribbean is a fantastic way to explore the region’s stunning natural beauty and vibrant culture. However, one consideration for sailors is the cost of marinas, anchorages, and moorings. In this chapter, we will discuss the typical costs of these amenities in the Caribbean and how they compare to other popular charter destinations.

Marina Costs

Marina costs in the Caribbean can vary widely depending on the location, facilities, and time of year. In general, marina costs in the Caribbean tend to be higher than those in other popular charter destinations like the Mediterranean or the Pacific. This is partly due to the high demand for marinas in the Caribbean during the peak charter season, which runs from November to April.

On average, marina costs in the Caribbean can range from $2 to $5 per foot per night, with some luxury marinas charging upwards of $10 per foot per night. However, it’s worth noting that many marinas in the Caribbean offer discounted rates for longer stays or off-season visits.

Anchorages and Moorings

While marinas can be expensive, anchorages and moorings are a popular and cost-effective alternative. Many areas in the Caribbean have designated anchorages and mooring fields where sailors can safely and legally anchor their boats for free or at a nominal cost.

In some areas, like the British Virgin Islands, there are private mooring companies that charge a fee to use their moorings. These fees can range from $25 to $45 per night, depending on the location and time of year.

The cost of marinas, anchorages, and moorings in the Caribbean is higher than in some other charter destinations. However, it’s important to remember that these costs can vary widely depending on the location and time of year. With some research and planning, sailors can find affordable and convenient options for their Caribbean sailing adventure.

Activities outside of Sailing

While sailing is the main draw for many travelers to the Caribbean, there are plenty of other activities to enjoy during your trip. From exploring historical sites to indulging in the local cuisine, here are some popular activities to consider on your next Caribbean sailing adventure:

Visit Historical Sites

The Caribbean is steeped in history, with many islands boasting museums, forts, and other landmarks that tell the story of the region’s past. In the British Virgin Islands, visit the ruins of the 17th-century Dutch-built Fort Recovery on Tortola or the copper mine ruins on Virgin Gorda. In St. Martin, visit Fort Louis, a 17th-century fortress overlooking the harbor, or the Museum of Saint Martin for a glimpse into the island’s history.

Explore National Parks

Many Caribbean islands have stunning national parks and protected areas, offering a chance to experience the natural beauty of the region. In the Bahamas, explore the Exuma Cays Land and Sea Park, which covers 176 square miles of pristine marine habitat, or take a hike through the Lucayan National Park on Grand Bahama Island. In St. Lucia, hike the Tet Paul Nature Trail for stunning views of the Pitons and the Caribbean Sea.

Sample Local Cuisine

The Caribbean is known for its vibrant cuisine, with dishes influenced by African, European, and indigenous cultures. From jerk chicken in Jamaica to conch fritters in the Bahamas, there’s no shortage of delicious food to try. Take a food tour in St. Martin to sample French and Creole-inspired dishes or try the national dish of Antigua, a spicy meat stew called pepperpot.

Relax on the Beach

The Caribbean is famous for its stunning beaches, with powdery white sand and crystal-clear waters. Spend a day lounging on the beach in the British Virgin Islands, where you can visit the famous Baths on Virgin Gorda or snorkel at Smuggler’s Cove on Tortola. In Grenada, head to Grand Anse Beach, a 2-mile stretch of pristine sand and turquoise water.

Go Diving or Snorkeling

With its crystal-clear waters and diverse marine life, the Caribbean is a paradise for divers and snorkelers. In Cuba, dive into the Bay of Pigs to see an underwater world of coral reefs, shipwrecks, and colorful fish. In St. Lucia, snorkel in the Anse Chastanet Marine Reserve, home to vibrant coral gardens and sea turtles.

Shop for Souvenirs

The Caribbean is a great place to find unique souvenirs and gifts. In St. Martin, browse the colorful markets in Marigot for local crafts and artwork, or head to the Arawak House of Culture in Dominica for handmade souvenirs. In the British Virgin Islands, visit the island of Jost Van Dyke, where you can find locally-made jewelry and crafts.

There is no shortage of activities to enjoy during a Caribbean sailing vacation. Whether you’re interested in history, food, or outdoor adventure, there’s something for everyone to experience in this beautiful and diverse region.

Pros and Cons of Chartering in the Caribbean

Chartering a sailboat in the Caribbean has its pros and cons. While the stunning scenery, consistent sailing conditions, and diverse culture make it a desirable destination for sailors, the high-season crowds, hurricane season, and higher costs may deter some.

• Beautiful Scenery The Caribbean boasts stunning turquoise waters, white sandy beaches, and lush greenery, making it one of the most beautiful sailing destinations in the world.
• Sailing Conditions The Caribbean offers consistent trade winds, calm seas, and warm weather year-round, making it a perfect destination for sailors of all skill levels.
• Island Hopping The Caribbean is home to over 7,000 islands, providing endless opportunities for island hopping and exploring new places.
• Diverse Culture The Caribbean is a melting pot of cultures, with a rich history and vibrant local traditions. Chartering a sailboat in the Caribbean provides an opportunity to experience a range of unique cultural experiences.
• Excellent Nautical Infrastructure The Caribbean has a well-established nautical infrastructure, with numerous marinas, anchorages, and mooring fields, making it easy to find a safe and secure spot to dock.
• High Season Crowds The Caribbean is a popular destination, which means that during the high season (December to April), the islands can be crowded with tourists, and marinas and anchorages can fill up quickly.
• Hurricane Season The Caribbean is susceptible to hurricanes, which occur from June to November, making it important to plan trips accordingly and purchase travel insurance
• Expensive Compared to other sailing destinations, chartering in the Caribbean can be more expensive due to the high demand and limited availability of boats during peak season.
• Limited Docking Options Some islands in the Caribbean have limited docking options, which can make it difficult to find a safe and secure spot to dock during peak season.

Caribbean Sailboat Charter: Conclusion

The Caribbean is a popular destination for sailing vacations, with its crystal-clear waters, stunning natural beauty, and rich culture and history. From island hopping and exploring ancient ruins to experiencing local cuisine and participating in cultural events, there is something for everyone to enjoy.

One of the biggest advantages of chartering a sailboat in the Caribbean is the diversity of sailing conditions and destinations, offering a unique and unforgettable experience. However, the cost of marinas, anchorages, and moorings can be higher compared to other charter destinations, which may be a consideration for some travelers.

Despite its higher costs, the Caribbean offers an unparalleled sailing experience with its warm waters, consistent trade winds, and stunning scenery. With its rich history, culture, and natural beauty, a sailing vacation in the Caribbean is an experience that will leave lasting memories for years to come.

Do I need a license to charter a sailboat in the Caribbean?

It depends on the country you plan to charter in. Some countries require a valid sailing license or certification, while others may not. It’s important to research the specific requirements for each country before booking your charter.

What is the best time of year to sail in the Caribbean?

The high season for sailing in the Caribbean is from December to April when the weather is generally dry and the winds are consistent. However, the shoulder seasons (May to June and November) can offer good sailing conditions and fewer crowds.

Can I bring my own food and drinks on board the charter sailboat?

It depends on the charter company and the boat you have booked. Some charter companies allow guests to bring their own food and drinks, while others may offer catering options or require guests to purchase food and drinks on board.

Are there any additional fees I should be aware of when chartering a sailboat in the Caribbean?

Yes, in addition to the cost of the charter, there may be additional fees for fuel, provisioning, taxes, and any optional extras such as water sports equipment or a skipper. Be sure to clarify all costs and fees with the charter company before booking.

What should I pack for a sailing vacation in the Caribbean?

Pack light, comfortable clothing that can be layered, as well as a hat, sunglasses, sunscreen, and insect repellent. Bring a waterproof bag or case for your valuables, and don’t forget to pack any necessary medications or personal items. It’s also a good idea to bring a pair of non-slip shoes for onboard safety.

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One of the world’s most desirable yachting destinations, the Caribbean captivates all who visit with its heady mix of natural beauty, calm waters and world class tourist amenities. For private yacht charter guests, the Caribbean is particularly well set up, with a vast number of charter companies offering yacht rental packages in the region.

Yachts anchored out in Salt Whistle Bay in the Grenadines (Photo: _dChris via Flickr / CC BY 2.0)

Whether you’re seeking a crewed yacht or a bareboat charter, a sailboat or a motorboat, there’s a huge choice of yachts available in the Caribbean. We’ve picked out 3 of the best companies currently operating that we’d recommend for Caribbean yacht charters.

Ritzy Charters

Charter with Sailo.com

Boat Bookings

Book at boatbookings.com

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• Sailboat rental in the Caribbean
• Boat rental
• Sailboat rental

Sailboat BENETEAU OCEANIS 48 14.63m 80hp  (2018)

Sailboat BENETEAU OCEANIS 41.1 12.43m 45hp  (2018)

Sailboat Bénéteau Oceanis 41.1 12.00m 45hp  (2018)

From $271 per day.

Sailboat Moorings 46.3 14.60m 57hp  (2019)

From $481 per day.

From $532 per day

From $593 per day

Sailboat Sunsail 51 15.38m 75hp  (2018)

From $923 per day.

Sailboat Sunsail 410 12.35m 40hp  (2019)

From $347 per day.

From $353 per day

Sailboat Bénéteau Oceanis 54 - 3 + 1 cab. 17.12m 110hp  (2024)

From $1,558 per day.

Sailboat Moorings 382 11.50m 29hp  (2018)

From $403 per day.

Sailboat Beneteau First 40.7 12m  (2008)

From $373 per day.

Sailboat JEANNEAU Sun Odyssey 349 - ZAURAK 10.34m 21hp  (2018)

From $717 per day.

Sailboat Beneteau Oceanis 48 14.00m 80hp  (2017)

From $1,159 per day.

Sailboat Moorings 42.1 12.43m 45hp  (2019)

From $459 per day.

Sailboat Sunsail 46 Mon 14.60m 80hp  (2019)

From $442 per day, explore the caribbean by sailboat.

There’s no better way to experience the Caribbean than by sailboat. With over 7,000 islands and islets, the Caribbean is a sailor’s paradise. The warm, turquoise waters and constant trade winds make it the perfect sailing destination. It's no wonder why so many people choose to rent a sailboat to island hop and explore this beautiful part of the world!

The Caribbean islands are home to some of the most stunning sailing destinations in the world. From the British Virgin Islands to Grenada , there’s a destination for every type of sailor. The white sand beaches and crystal-clear waters are breathtaking, and the lush tropical landscapes are simply unforgettable. Whether you’re looking for a romantic getaway, a family vacation, or a sailing adventure with friends, the Caribbean has it all.

Chartering a sailboat in the Caribbean is easy with Click&Boat. We offer a wide variety of sailboats to choose from. Our charter fleet includes boats of all sizes, so whether you’re traveling solo or with a large group, we’ve got you covered. Connect with local Caribbean sailboat owners to create your dream sailing experience.

With Click&Boat, you can find the perfect boat for your needs and budget. Use our price filter when searching for your sailboat rental in the Caribbean to find one that fits within your budget. Don't miss out on the opportunity to explore the Caribbean by sailboat!

Why should I rent a sailboat in the Caribbean?

There are many reasons why renting a sailboat in the Caribbean is the perfect way to explore this beautiful part of the world. First and foremost, sailing is the best way to experience the Caribbean's natural beauty. With so many islands and islets to explore, there's always something new and exciting to discover. Whether you're looking for a secluded beach, a hidden cove, or a lively port town, a sailboat gives you the freedom to explore at your own pace.

Sailing in the Caribbean is also an incredible adventure. The constant trade winds make perfect sailing conditions, and the warm, clear waters are perfect for swimming, snorkeling, and diving. With so many islands to choose from, you can plan your perfect sailing itinerary, and experience a different island and culture every day.

Click&Boat has ideal sailboat options for you, no matter if you’re an experienced sailor or a novice with the option to rent with or without a captain. Whether it’s your first time stepping on a sailboat or if you are an expert sailor, you can find a boat that suits your needs.

How much does it cost?

The cost of renting a sailboat in the Caribbean varies depending on several factors, including the location, the length of rental, the size and make of the sailboat and more. Generally, the cost of renting a sailboat for a day in the Caribbean can range from $300 to $800, depending on the boat's size, features, and location. For a week-long rental, the cost can range from $2,800 to $4,200, on average.

It's important to note that the cost of renting a sailboat in the Caribbean can vary significantly depending on the time of year you plan to sail. During peak season (typically November through April), prices tend to be higher, while off-season rentals can be more affordable. Additionally, some locations, such as the British Virgin Islands, may have higher rental prices due to their popularity and limited availability.

When renting a sailboat in the Caribbean, there may be additional costs, such as captain and mooring fees. However, despite these additional costs, renting a sailboat in the Caribbean can still be a one-of-a-kind way to experience this beautiful part of the world.

When is the best time to go?

Sailing in the Caribbean is possible year-round, but the best time to go depends on your preferences and priorities. If you're looking for calm waters and consistent weather, the best time to go is during the high season, which runs from December to April. During this time, you can expect dry weather, calm winds, and clear waters, making it the perfect time for island hopping and exploring the region's stunning beaches.

However, if you're looking for a more affordable and less crowded sailing experience, the shoulder season (May to November) might be a better option. While you might encounter more rain and occasional tropical storms during this time, you'll also enjoy lower prices on yacht charters and have more anchorages and beaches to yourself.

The harbors in the Caribbean

The Caribbean is known for its stunning beaches, balmy weather, and vibrant culture. But it's also a great place to go sailing and explore the many islands of this beautiful region. If you're looking for a sailboat charter in the Caribbean, there are plenty of options to choose from.

Here is a list of different harbors and marinas where you can dock your boat and enjoy exploring the Caribbean:

• Simpson Bay Yacht Club & Marina: This marina on the Dutch side of St. Martin is a great starting point for exploring the beautiful waters of the Caribbean.
• Rodney Bay Marina: Located in St. Lucia, this marina is a popular destination for sailors, offering easy access to nearby attractions and beautiful anchorages.
• Antigua Yacht Club: This historic yacht club in Antigua is a must-visit for sailors, with a beautiful clubhouse and world-class facilities.
• Soper’s Hole Marina: This marina in Tortola is a popular destination for sailors in the British Virgin Islands, with its lively atmosphere, restaurants, and easy access to nearby beaches and anchorages.
• Blue Lagoon Marina: Situated in St. Vincent in the Grenadines, this marina is a popular destination for sailors, with its beautiful scenery, nearby beaches, and access to stunning sailing destinations like Bequia and Mustique.

What are the best places to sail to in the Caribbean?

The Caribbean is home to some of the most beautiful sailing destinations in the world, with a wide variety of islands and destinations to explore. Whether you're looking for secluded beaches, lively towns, or stunning natural beauty, there's something for everyone in the Caribbean. Here are some of the best places to sail to in the Caribbean:

• Antigua : Known for its 365 beaches, Antigua is a popular destination for sailors looking to explore its turquoise waters and charming towns.
• St. Lucia : This lush island boasts stunning natural beauty, from its iconic Pitons to its black sand beaches and rainforest.
• Tobago Cays: This group of small, uninhabited islands in the Grenadines and St. Vincent is a true paradise, with crystal-clear waters and plenty of opportunities for snorkeling and diving.
• British Virgin Islands: A sailor's dream destination, the BVI offers everything from secluded anchorages to bustling beach bars and restaurants.
• Grenadines: This chain of islands is known for its pristine beaches, crystal-clear waters, and laid-back vibe, making it a perfect destination for a relaxing sailing vacation.

Other great destinations to explore in the Caribbean include the Bahamas, St. Martin, the Dominican Republic, and many more. No matter where you choose to sail in the Caribbean, you're sure to have a memorable experience.

Renting a sailboat with or without a captain

Another great reason to charter a sailboat in the Caribbean is the availability of skippers. If you're new to sailing, a captain can make all the difference. They'll know the best spots to go and which tides to avoid, so you can focus on enjoying yourself. Plus, they'll handle all the logistics so you can just enjoy the sailing.

But if you're an experienced sailor and are looking to take full control of your vacation and enjoy the open sea, you should consider going on a bareboat charter! Before setting sail make sure you have the right documents.

What brands or models can I rent?

Whether you choose to charter with a private or professional owner, a sailboat rental in the Caribbean has never been so easy. With Click&Boat, the world’s leading boat rental service, book the boat of your dreams whether it be a bareboat charter or a crewed yacht!

Rely on the best prices, an internal messaging tool for owners and renters, as well as a knowledgeable team of advisors ready to help- because booking shouldn’t be a hassle.

Choose to set sail with your favorite shipyard Jeanneau, Beneteau, or DuFour, and discover the islands of the Caribbean, in comfort and style.

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Home » Destinations » Boat rental » Sailboat charter » Caribbean

Sailing in the Caribbean is a dream of many sailors. The beautiful sea, the trade wind and the pleasant waters are ideal for a sailing vacation, not to mention the fact that navigating amongst the many islands here is quite exciting. The ports and islands in the Caribbean are ideal for those who love adventures, beautiful sights, and hotness.

Read more information about sailboat charter in the Caribbean on the following tabs: About Caribbean , Caribbean weather . Get some inspiration from the Caribbean itineraries tab and start planning your next sailing itinerary, read detailed descriptions of Caribbean sailing destinations , or Caribbean sailing articles.

The most popular Caribbean sailboat charter destinations

About caribbean, caribbean weather, caribbean itineraries.

Antigua sailboat charter

Bahamas sailboat charter

BVI sailboat rental

Grenada sailboat charter

Sailboat charter Guadeloupe

Martinique sailboat charter

Sailboat charter Mexico

Sailboat charter USVI

Location of the Caribbean

The phrase, Caribbean region, stands for the North and Central American groups of islands. In a broader sense, some Central and South American countries also belong here, such as Columbia or Venezuela. There are more than 700 islands in the region. We can divide the Caribbean Islands into three main parts. The Bahamas, the Greater Antilles, and the Lesser Antilles.

Beaches in the Caribbean

There are several gorgeous beaches, gulfs, and lagoons here. The crystal clear seawater and warm sunlight create a picturesque view. The beauty of the landscape will surely make your travel memorable. The white sandy shores of the Caribbean Sea are among the most astonishing swimming sites in the world. Here are some:

Gulf of Maundays, Anguilla

One of the most popular holiday resorts, Cap Julica is in this gulf. The amazing five-star resort provides full comfort and luxury. Thus, no wonder celebrities also like staying here. The beach has a private bar and other services as well.

Valley Church, Antigua

A cosy beach that enchants visitors with different shades of blue water. The water is calm and crystal clear, white sand carpet covers its shore. You can discover hundreds of other beaches between Antigua and Barbuda. They will certainly outshine your expectations. The secret gems of this area are its hidden gulfs, which you too can explore if you rent a boat.

Pink Sands beach

Many visit Harbour Island to view this famous section of the seaside. The coral is a unique mixture of broken shells, miniature stones, and calcium carbonate. It colours the sand with pink fragments. It’s a wide and long beach surrounded by calm water. It can be an ideal and beautiful venue for wedding ceremonies, sports, or yoga.

Treasure Beach, Bahamas

It’s among the best beaches in the world. Treasure beach is a 3, 5- mile -long section of the shore with every service available to make a vacation incomparable and even more excellent. You can enjoy pleasant cafés and restaurants or try watersports.

Main attractions in the Caribbean

The picturesque scenery welcomes visitors with several colourful and unique programs. Besides beautiful beaches, you can take pleasure in viewing the exotic flora of the jungle or the underwater wildlife. Sea turtles are amazing residents of the Caribbean Sea. They are one of the endangered species, thus, numerous rescue and breeding programs started in the past few years to protect the animals. Many visitors come to Puerto Rico to see the turtles, while they’re laying their eggs in the sand. They also come to see the exciting moment, when the little turtles leave their nests and go into the water. Besides water and seaside sights the Caribbean region also has a rich cultural heritage. There are more than 40 museums in Cuba, that display art, music, the revolution, chocolate, or cigars.

The Caribbean weather

The Caribbean region has the traits of all year hot and humid tropical climate. The weather is somewhat cool and dry from the middle of January to the middle of April. From the middle of June to the middle of November it’s usually hot, wet, and rainy. Subtropical monsoon climate dominates in the region. The average yearly temperature is 28 °C.

Sailboat charter in the Caribbean

A roundtrip on the Caribbean Sea could be a very exciting and memorable program for the whole family. Rent a small boat, a luxury yacht, or a sailboat. It’s important that you find out about landing places. The Caribbean region involves numerous ports, small and large. However, they might be very different. The most popular and high-standard ports are in the larger cities. These are the ports of for example Nassau, Falmouth, Puerto Rico, Philipsburg, or Mexico. They are well-equipped and provide all the services necessary for boating. The majority of sea centers and smaller islands are in daily connection.

The most popular ports in the Bahamas

Great guana cay.

Great Guana Cay is located in the centre of the Exumas. It has two great anchorages: Black Point and Little Bay. Black Point is a true gem with a nice port and several moorings. People are very friendly and casual, and they find it important to help sailors in any way they can. Little Bay is a small bay at the southern end of Black Point. The sea bottom is sandy, making it ideal for securing our boat safely. The depth of water is app. 3-4 metres. There is a beautiful beach here, but there are no establishments, ports or shops. Information about Exumas sailing or boat rental in Exumas

Spanish Wells

Spanish Wells is located on St. Georges Cay, west of the northern corner of Eleuthera. Its port is constituted by a long channel bordered by two small islands. It is protected well and is only open for the winds coming from the eastern direction. There is a great port and a hurricane hole in the west where boats are tied to mangrove trees. There are six anchoring buoys on the eastern side. We can find Spanish Wells Yacht Haven & Marina here which is a full-service yacht marina with 40 berths; besides the basic services, they also have a bicycle rental.

The downtown is within walking distance. We can anchor at Royal Island Harbour in the west, which provides ideal anchorages for vessels with a larger draft. The only disadvantage is that they have no amenities or services. Information about Eleuthera sailing , or boat rental in EleutheraMore about Bahamas sailing tours, or Bahamas yacht rental

The most popular ports in the BVI

Nanny Cay is located on the southern coast of Tortola. It is located a little over 3 kilometres from Burt Point. At this port, we have the opportunity to pull our boat from the water, among other services. Nanny Cay Marina offers 320 berths; 120 on the outer parts and 200 in the inside. They provide access to fuel and electricity in both areas. We need to pass through a narrow route for entry.

Road Harbour

Road Town is the capital of Tortola and the sailing centre of the British Virgin Islands. We can enter the port through the Sir Francis Drake Channel . Road Harbour has several yacht marinas providing full service and accommodation. We can find Road Reef Marina, Fort Burt and Wickham’s Cay I and II here; Road Reef Marina and Fort Burt are on the western side, while Wickham’s Cay is on the north. There are over 120 berths and downtown Road Town can be found nearby. Many sailors start their trip here when visiting the British Virgin Islands. Information about sailing in Tortola , or boat hire in Tortola

Virgin Gorda Yacht Harbor és St. Thomas Bay

The Virgin Gorda Yacht Harbor is in St. Thomas Bay. It is easy to approach it, we only have to sail the marked channel. The harbour is beautiful, offering great services and marine gas. There are 100 berths, and it is possible to stay for only a few hours, a day, or long-term as well. It is close to the centre of Spanish Town. It is a very peaceful town where you can find many shops, restaurants, and bars. One of the most famous attractions of the town, The Baths, is about 3 km from here. This is a collection of granite rocks on the beach that have become large rock formations. The rocks from tidal basins, channels, and spectacular caves open to the surrounding waters. Information about Virgin Gorda sailing , or Virgin Gorda boat chartersMore about BVI sailing routes , or BVI boat rental

The biggest ports in Puerto Rico

San juan cruise port.

With two terminals, San Cruise Port is one of the largest and busiest ports in the Caribbean. The two terminals can accommodate up to 9 cruise ships at the same time. Due to its geographical location, the port is safe even during hurricane season. The port offers several services like towing, drinking water access and electricity, telecommunication services and shops. The city’s tourist attractions are easily accessible by public transport.

Marina Puerto Chico ( Fajardo )

The marina of Fajardo is located on the east coast of Puerto Rico. It is a natural, quiet coast, and the depth of the water is 5-6 m. Despite its small size, it has a great infrastructure: water, electricity and refuelling are available. You can easily visit Culebra, Vieques and the British Virgin Islands from here.

Port of Mayagüez

The third busiest port in Puerto Rico is northwest of downtown Mayagüez, stretching for 6 km along the coast. The depth of the water is 8-9 m. Despite being one of the smaller ports, it can accommodate boats up to 150 m in length. The communication infrastructure is also outstanding. More about Puerto Rico sailing, or boat rental in Puerto Rico

The most popular ports in Mexico

La Paz is the most city in southern Mexico on the Baja California Península. It has several ports.. One of the best-equipped ports is Marina Cortez, located in the heart of the bay. It offers a number of exclusive services for even the largest sea yachts.

The city’s port, called El Cid, is way more than a simple landing opportunity. There is a bustling market and several miles of nearby beaches with golden sand. The local dive shop is excellent, you can get all the necessary equipment here. In the port area, you will find plenty of high-quality accommodation opportunities. More about Mexico sailing , or boat rental in Mexico

The biggest ports in Cuba

Port of cienfuegos.

The main port in the southern part of the island is La Perla del Sur or the Pearl of the South. The port of Cienfuegos is considered a large port in Cuba. It can accommodate boats up to 150 m. The depth of the seabed is 12 m. While Christopher Columbus visited in 1494, it was formally founded in 1819.

Port of Santiago de Cuba

The second-largest port city of Cuba is located in the southeastern part of the island, in Oriente Province. It is a major port for import and export in the region. The bay is quiet and protected against winds. The famous Casa del Habano is a few-minute walk from the port. Here, you can buy the best-quality Cuban cigars and you can visit the Bacardi Museum. More about Cuba sailing, or boat rental in Cuba . Another option is to explore the sea by yourself on the deck of a yacht charter. If your only wish is an amazing sea vacation, or the presence of stunning natural wonders, visit the Caribbean Sea to find all of these.Find sailing routes in the Caribbean .

More information about the Caribbean

Caribbean sailing routes & Caribbean sailing destinations Sailing destinations & Sailing routes

Sailing in the Caribbean: an unforgettable experience for you. Caribbean sailing trips

Sailing in the Caribbean is a dream of many sailors. The beautiful sea, the trade [...]

For more precise information about the Caribbean area,  please narrow down your search. It is necessary in this case, because of geographic diversity and the large scope of the area. First select a destination on the sailboat charter in the Caribbean tab and choose the Weather tab of the selected area and read the related description.

Rent a sailboat in the Caribbean, and cruise around the Caribbean

Puerto rico sailing itineraries.

Bahamas sailing itineraries

Antigua sailing itineraries

BVI sailing itineraries

Read about sailing to the BVI , BVI sailing itineraries , or BVI sailing routes..

Cuba sailing itineraries

Read more Cuba sailing itineraries , or choose from Caribbean sailing destinations .

"If you rented a boat from us, we don't need to introduce ourselves. If you book with us for the first time, you will soon get to know us." 🙂 Some feedback about us...

Lavrion - Greece

Sehr guter Service und Beratung. Die Buchung war recht einfach.

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Milos - Greece

Our catamaran sailing trip was fantastic. The Alegria is an amazing boat. Comfortable and beautiful, with all the features one could hope for...

Harry (USA)

Dubrovnik - Croatia

Ismét nagyon jó áron kaptunk,egy igazán luxus hajót. A Bali 4.5 egy igazán jó válaasztás. A Köszönjük az ügyintézést.

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Mykonos - Greece

Easy to book, and perfect communication from the very beginning. The boat was in perfect condition and very comfortable for a group of 10pax...

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Sevice Types

Yacht builder year: ascending Yacht builder year: descending Price: low to high Price: high to low Length: ascending Length: descending Berts: ascending Berts: descending Capacity: ascending Capacity: descending Number of cabins: ascending Number of cabins: descending

Dufour 41 (2024)

Bahamas, Mars Harbour (Sailing yacht)

from 949 € /day  

View details

Oceanis 40.1 - 3 cab. (2023)

Caribbean, Grenada (Sailing yacht)

from 653 € /day  

Dufour 470 - 5 + 1 cab. (2023)

Caribbean, Guadeloupe (Sailing yacht)

from 560 € /day  

Dufour 430 GL (2023)

from 729 € /day  

Dufour 390 GL (2023)

British Virgin Islands, Tortola (Sailing yacht)

from 631 € /day  

Sun Odyssey 410 - 3 cab. (2023)

from 6 454 € /day  

Sun Odyssey 410 - 3 cab. (2022)

Bahamas, Nassau (Sailing yacht)

from 824 € /day  

Sun Odyssey 440 - 3 cab. (2022)

from 761 € /day  

Jeanneau 54 - 5 + 1 cab. (2021)

from 786 € /day  

Sun Loft 47 - 6 + 1 cab. (2020)

from 664 € /day  

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Your Captain and Chef Charter

Captained sailing vacation.

Vacations are meant for relaxing and being afloat is no exception. Taking a charter skipper for a captained sailing vacation will allow you to fully enjoy your time on board without having to worry about itinerary, safe anchorages or systems on board. Even for the most experienced sailor, it’s nice to have some time for your mind to switch off!

This is your vacation, you can choose how involved you would like to be in planning the itinerary, hoisting sails or taking the helm. With a captained sailing vacation you can use your valuable skipper’s expertise to expand your own knowledge, and swap your best sailing stories and tips. Your skipper can be involved in your vacation as much or as little as you would like. It’s no problem to spend an evening ashore with family and friends, your skipper will make sure your vessel is safe and your cabins cool and air-conditioned for your return. If you are fascinated by the underwater world, then let your skipper guide you to the best snorkelling spots to point out lobsters hiding under rocks and lesser spotted marine life.

Enjoy all those painkillers with the knowledge that you’re not driving the dinghy at the end of the night. If you’d rather be in a bay with no one else around then your skipper can take you to spots that charter guests cannot reach so you have that unlit view of the milky way. If you’re looking for added adventure your skipper can show you hiking trails for exclusive island views, organize kiting lessons or take competent kiters to safe spots to launch from.

We pride ourselves at Horizon in only offering skippers that give you the full package. Our skippers are sailors, engineers, riggers, tour guides, entertainers, cocktail makers, deck washers, and DJs and will very likely be friends by the end of the trip.

If your idea of a vacation means staying out the galley during your trip then why not hire your own private chef for the week? Breakfast, lunch, and dinner are tailored to your personal taste. Your skipper and chef will work together to match food and itinerary whether that be local grilled fish Al Fresco under the stars or Jerk chicken wraps underway. Our chefs prepare a range of breakfasts, from tasty omelettes and French toast to more continental-style platters. Fresh local fruit is in abundance. Dishes could include blackened tuna, BBQ spicy steaks or Caribbean-inspired gumbo. To go along with this feast, you will have salads and other sides. Dessert could be something chocolatey and gooey; the best kind, or a cheese and fruit platter. We serve meals with a range of beverages, from healthy smoothies to wonderful wines.

If you would like to come away from your trip with ASA certifications, then check out our Horizon Sailing School page for more information.

Check out skipper

You’ve been up all day travelling and you’ve made it to paradise but now you’re boarding a boat you’ve never been on, on unfamiliar islands and suddenly you’re faced with hundreds of anchorages to choose from, water makers and in-mast furling systems.

Rather than spending your first day on the dock working out how everything runs, why not take a check-out skipper who can talk you through the systems as you use them?

Has it been a while since you picked up a mooring ball? Your check-out skipper can make sure that the first pick-up goes smoothly. Unsure about your itinerary? Go over the chart whilst watching the sunset and get real local knowledge on where to explore. Is this the biggest boat you’ve been on? Or have you spent years on a monohull but never manoeuvred a cat? Your check-out skipper can guide you through docking and moving in close quarters to build confidence for the week ahead. Taking a check-out skipper to your first anchorage or for the first 24 hours of your trip is the best way to start your vacation smoothly and settle into island time.

Call Horizon Yacht Charters now with your requirements, or Request a Quote here ,  and we will tailor-make the Caribbean sailing vacation of your dreams.

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New to the Yacht Charter Fleet

• By Yachting Staff
• March 21, 2024

Several of the world’s leading charter-management companies have welcomed new yachts into their fleets, with inquiries for bookings now being accepted.

Althaus Yachts has added the 116-foot Azimut Grande 36 Ocean One to the charter fleet in the Mediterranean. This yacht is a brand-new, 2023 build that comes with quite the sexy tender: a 60-knot Brabus Shadow 900 Sun-Top Stealth Green Signature Edition. Ocean One can accommodate 12 guests, and has guest amenities including an infinity pool.

Also new to the fleet, with Fraser, is the 132-foot Aegean yacht Donna Del Mare . This yacht is currently completing a refit, with charters expected to be available in the Adriatic Sea between early April and mid-September. Accommodations are for 12 guests along with four supernumeraries such as nannies and bodyguards. Guest amenities include two bars and a sundeck hot tub.

Fraser is also now offering the 156-foot CMB Fortuna for charter in the Mediterranean. This 2023 build has an Espen Øino exterior, interiors by Art-Bel Design, and accommodations for 10 or 11 guests in five staterooms. Guest amenities include a hot tub, barbecue, DJ console, gymnasium and waterside beach club. A 43-foot Venom chase tender is part of the charter package.

Also new to the charter fleet is the 146-foot Intermarine Artemisea , which IYC is offering in Greece. Accommodations are for 10 guests in five staterooms, including a full-beam master. This yacht underwent what IYC calls a major refit this year. Guest amenities include a sundeck hot tub, and IYC says the yacht’s fuel consumption is low.

IYC’s offerings in Greece also now include the 108-foot Lurssen Alaya , which is a classic build from 1965. Alaya was “meticulously refitted” in 2023, according to the charter company, creating the combination of a classic yacht with updated, modern comforts. The original owners modeled the yacht after World War II torpedo boats, giving the yacht a touch of history as well. Accommodations are for 10 or 11 guests in five staterooms, and the owner will consider inquiries for corporate or personal events.

But wait, there’s more: Also new to the charter fleet, with Edmiston, is the 154-foot Feadship Lady Victoria . This 2015 build, which is accepting inquiries for the Caribbean, was most recently refitted in 2022. Accommodations are for 12 guests in their choice of seven staterooms, with interior design by RWD. Exteriors on this yacht are by Dubois.

How to book a week on board: contact a charter broker at althausyachts.com , fraseryachts.com , iyc.com or edmiston.com

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From the US Virgin Islands to Aruba, Caribbean Travel Is Booming

The Caribbean’s Must-Visit Yacht Show Is Coming to St Thomas 

The Virgin Islands Boating Expo will take place May 10-12, 2024 at Yacht Haven Grande St. Thomas, the USVI’s top yachting destination.

This boutique destination show, hosted by the Virgin Islands Professional Charter Association, ticks the top three boxes of what yacht buyers today want in a yacht sales experience: the ability to yacht shop, wine and dine, and stay and play — making for a unique kind of boat show-meets-food-festival event.

“We welcome our attendees, both the public and those flying into our award-winning destination, to visit with yacht dealers, manufacturers, exhibitors, and our local and global vendors,” said Joseph Boschulte, USVI Commissioner of Tourism. “Experience the best of what the U.S. Virgin Islands offers on land and sea and shop for a yacht while you’re here.”

Yacht shoppers can take advantage of duty-free tax benefits when buying in the USVI.  

It’s another major event for the Yacht Haven Grande Marina, which saw a major boom during the pandemic and continues to be a premier yachting jump-off point in the broader region.

The Government of the Virgin Islands also supports infrastructure on shore to maintain charter business interests such as an Economic Development Commission Tax Incentive Program for charter yachts. 

Charter company professionals, financial companies and Marine Expo vendors with global and local products will be on hand to talk about charter management opportunities in the USVI.

The latest models of top brands will be on site, including Bali, Lagoon, Fountaine Pajot, Leopard, McConaghy, Azimut and Boston Whaler, to name a few. 

Yacht buyers benefit from St. Thomas as a hub destination for transport ships delivering yachts from foreign manufacturing facilities. 

Attendees can walk the docks, tour the yachts, meet the professional crew and receive a fully immersive experience on board, with the opportunity to test-sail directly from the show berth through the scenic Charlotte Amalie harbor to world-class cruising grounds.

“Teaming up with Waypoints Yacht Charters, our luxury yacht charter sister company, we will bring attendees a dynamic duo that not only meets but exceeds market expectations,” said Laurent Fabre, vice president of sales and marketing for Fort Lauderdale, FL-based Atlantic Cruising Yachts, which will feature two stunning Fountaine Pajot catamarans, the Aura 51 and Alegria 67. “Discover the epitome of luxury and performance as our Yacht Consultants unveil the revolutionary Fountaine Pajot Smart Electric propulsion system, designed to enhance the experience for private owners and elevate charter fleet operations.”

Daily yacht viewings combine with live music and cultural performances, starting with the Exhibitor’s Opening Ceremony & Reception on May 9, from 5-7 p.m.

VIBE and Cutlass & Cane, Yacht Haven Grande St. Thomas’ newest restaurant, have partnered to produce a curated Food & Wine Experience, with lunch served daily from 12-3 p.m. including wine pairings. 

Yacht Haven Grande is also home to Blue 11, which has been featured in the 50 Best Restaurants in the Caribbean ranking.

All attendees can also visit a variety of pop-up bars featuring many beverages distributed by West Indies Company, including St. Croix, U.S. Virgin Islands-made Mutiny Island Vodka, the world’s first and finest Island Vodka made from breadfruit and Caribbean rainwater and St. Thomas-crafted Leatherback Brewing Company’s products, which offers craft beer made with Caribbean-grown ingredients.

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