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Catamaran Sailing Vacations in Florida Keys: Upper and Lower Florida Keys - Dry Tortugas - Fort Lauderdale, Miami, Marathon and many different stops along the way! Charter a Catamaran with no crew and drive yourself or hire professional crew for your catamaran trip.

The florida keys have become a popular destination for americans looking for a tropical sailing vacation without leaving their own country. the florida keys can be considered the american caribbean and features all the same amenities as other island destinations such as world class sport fishing, scuba diving and snorkeling, boating, sailing, kayaking and eco-tours. each of the island destinations has some special features. we invite you to visit each area individually and discover the tropical paradise in the florida keys..

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Catamaran Sailing Vacations Florida Keys

Florida Keys Itinerary

Keys - one week.

Catamaran Sailing Vacations with crew

Upper Florida Keys - 3 Days

Lower Florida Keys - One Week*

Sailing from Marathon Key you will experience the many pleasures and sites of the Florida Keys. The unspoiled coral reefs of the Lower Keys have many sites where you can tie up to a mooring ball and snorkel or dive. Hawks Channel provides fantastic sailing, as there is protection from the ocean swells but still great wind.

Dry Tortugas - One Week*

Bahamas itinerary, chain in the bahamas.

Across the Gulf Steam from Florida's east coast lies the Bimini Island Chain. These sub tropical low-lying islands are a fantastic destination for a weeklong sail. Bimini offers some of the finest SCUBA diving, snorkeling, fishing and beachcombing anywhere. These "islands in the stream" offer water clarity, which is nothing less than spectacular. You may rent snorkel gear at our office in Ft. Lauderdale if you have not brought your own. For those who are certified divers we recommend renting your SCUBA gear from Underseas Sports in Ft. Lauderdale before you head across the Gulf Stream.

The Bimini Chain is lightly populated with the center of village life located on North Bimini, in Alice Town. There are many small restaurants, shops, and bars, as well as the Hemingway Museum at the complete Angler. Marinas are abundant if you decide not to anchor out. The beaches on North Bimini offer miles of un-crowded fine white sand and snorkeling from the waters edge. Golf Carts and Mopeds are available for rent so you can explore the island. One of the most interesting dive and snorkel sites off of North Bimini is "Bimini Road", which some say is the ruin of the lost city of Atlantis.

South Bimini is primarily residential with only two marinas. The new Bimini Sands Marina is located at the entrance to the harbor and has a Customs and Immigration office so you can clear in there without having to take a taxi and ferry over to North Bimini. The other marina is located at the south end of the island. A new channel has been dredged in Nixon's Harbor that takes you into the marina. Not far from the south end of South Bimini lies the wreck of the "Sappona". This is a great snorkel and dive site.

The only other island in the Bimini's with a marina is on North Cat Cay. This is a private Island with some "high profile" homeowners. For this reason the local authorities limit the accessibility of the island for non-members. You are welcome at the Marina for transient dockage but they prefer for you to stay in the area of the marina where there is a fine dining restaurant a store for provisions, dock bar, and gift shop. It is a truly beautiful setting at the marina and we recommend this for your last night in the Bahamas. Just off the coast of South Cat Cay is a fantastic dive site. "Tuna Alley" has mooring balls and is 50' to 80' with deep caverns and crevasses in the coral.

There are many other Anchorages such as Honeymoon Harbour, Dollar Harbour. Moxom Rocks, and Nixon Harbour. Please call to speak with our knowledgeable staff for more details.

One Week Itinerary to the Bimini Islands

Day three -, day seven -, day eight -.

Obviously there can be a lot of variation on this itinerary, but it shows there is plenty to do in a week charter to the Bimini Island Chain. If you would like further information or would like to plan a different Bahamas trip give us a call and speak with our knowledgeable staff. We can provide you with a cruising guide to the Bahamas Islands as well as charts of the area.

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…is a fast and comfortable sailing machine, providing the most stable ride on the water. naturally it’s a catamaran.

And with our big bimini top, you can get all the Key West sun or shade that you want. The fresh water shower on deck comes in handy on those hot days. A private bathroom in the cabin makes a day in the wildlife refuge civilized and helps protect our tropical waters.

ECHO is located at the “Key West Historic Seaport” which is downtown in Old Key West at the famous Key West Bight. The Historic Seaport “Harbor Walk” goes right around the water’s edge and leads right to ECHO‘s dock along side the famous “Turtle Kraals Restaurant and Tower Bar”. Spend the day on the Harbor Walk before and after your ECHO trip and visit all the great shops, restaurants and bars and galleries. This is where all the locals hang out!

So come and hang out in the coolest part of town and cruise with us at Catamaran ECHO .

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Experience the beauty and wonder of an unspoiled tropical paradise without ever leaving the Continental United States. Our Key West sailing charter destination is located minutes from all the downtown Key West attractions and Duval Street night life, yet a short sail away from pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas. Kayak, paddle board, and snorkeling excursions will open to you the offshore beauty offered only in the Florida Keys. Our native Floridian staff knows how to find the best activities on land or at sea, to guide you as you plan a unique and customized getaway.

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Historic Duval Street

One of the most popular destinations on the island of Key West is Duval Street. Visit the Ernest Hemingway Home and Museum where you can take in some history about the writer and meet a legendary six toed cat. If you feel like taking in some nature, visit the Key West Butterfly and Nature Conservatory where there are 50 - 60 different species of live butterflies from around the world. On Duval Street, you can simply take a stroll and hear live music, see art galleries, enjoy coffee shops and great restaurants, or find unique souvenirs at one of the many boutiques.

Romantic Sunsets

Beautiful sunsets are what Key West is all about. Enjoy the soothing ocean breeze, a glass of wine, and relax to the backdrop of the setting sun on your own private catamaran cruise. Watching the sunset has become an integral part of everyday life in paradise. This is one tradition you don’t want to miss!

Key West sunset

Crystal Clear Snorkeling

Key West offers many beaches and reefs where you can experience snorkeling in warm crystal-clear water. At Cottrell Key, see the unique sponge garden and large coral reefs. It is also an excellent place to see dolphins, sharks, stingrays, and Goliath groupers. Fort Zachary Taylor is considered one of the best offshore snorkeling spots in Key West where there are a variety of tropical fish species and living coral to see. A favorite among snorkeling enthusiasts is Sand Key Lighthouse Reef. With a remote location and strict no-take policy, the Sand Key Lighthouse Reef is one of the healthiest coral gardens in Florida.

Pristine Sandy Beaches

Craving a drink in your hand and your toes in the sand? Check out the turquoise waters at Smathers Beach. Rental shops are available with beach chairs, shade umbrellas, kayaks, jet skis and much more. Try South Beach for calm, shallow waters that are excellent for swimming and great for families. Higgs Beach is unique for its historical significance. Take a wander around, and you'll find monuments dedicated to the 19th-century slave cemetery located on the site. There is also a pier at Higgs Beach, where visitors can often spot stingrays and other marine species.

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Get Away to Key West and Explore the Florida Keys by Sailboat

Did you know there's an international airport perched out in the Gulf of Mexico at Key West? Serviced by all major US airlines and with frequent flights from main airports in the East and South, Key West is so easy to get to. That's where you'll find our boat charter operators, who have a range of sail and motor boats for you to explore this unique corner of the USA.  

Along the Florida Keys the holidaymaking options are numerous. Enjoy the aquatic environment with countless opportunities to snorkel, swim, kayak, paddleboard and more, while totally relaxing on board, or ashore on one of the Keys' beautiful beaches. Enjoy an evening meal in one of the upmarket restaurants that dot the Keys, shop and enjoy the nightlife in the major centers of population, and get close to nature at one of several locations designated State Parks. 

While pandemic concerns are limiting travel options, consider Key West as your next boat charter vacation destination. Local ordinances reflect the need to keep everyone protected and make this a safe destination. The communities are welcoming and open for business. 

catamaran sailing florida keys

Some of the highlights to experience on a Florida Keys Sailing Charter Vacation 

Your Florida Keys adventure likely begins and ends at Key West, which is closer to Cuba than Miami yet connected to the US mainland by the 90-mile long Overseas Highway that's an experience in itself. Most sailing charter visitors arrive by air and take the short transfer to one of the charter bases located on the island. Famous for its coral reefs, local architecture, historic sites and nightlife, charming Key West is well worth some time before or after your charter.  

Like most charterers however, you will probably be keen to go sailing and start exploring the chain of cays that make up this most southerly part of the Continental USA. Two great things about sailing here are that distances between attractions can be as short as you'd like them to be, and anchorages are plentiful, if shallow in places. A seven-day charter Key West to Key Largo and return is easily achievable. 

Travelling out of the Stock island marina, it's less than 30 nautical miles to Baihia Honda Key, a popular stopover. In the vicinity there's a variety of stunning beaches, some say the best in the world. Looe Key has some of the best snorkelling you'll experience on your vacation. 

A similar distance to that travelled above will take you from Bahia Honda Key to Long Key, via Marathon, a major sport fishing town of 10,000 people surrounded by the bountiful sea. Stop a while and enjoy a seafood lunch, or you may prefer to do Marathon on the return. At Long Key enjoy the natural surroundings, the greenery and the birdlife. 

Perhaps after two days of sailing that have taken you from Key West more than half way to the mainland, you're ready to take it a bit easier. Less than ten nautical miles onward you'll come to Indian Key Historic State Park at Islamorada. Nearby is the San Pedro Underwater Archeological Preserve, another one of the numerous state parks along the Keys. The San Pedro was a Dutch ship sunk during a hurricane in 1733. What remains lies in 18 feet of water 1.25nm south of Indian Key, easily accessible to good swimmers. 

From Indian Key, it's a further 20nm sailing distance to Key Largo. Apart from the shops, bars and restaurants, most of the attractions are aquatic-based as they are all along the Keys. A visit to the Florida Keys Wild Bird Rehabilitation Center can be rewarding, a reminder of the fragility of nature in this delicate place. 

If you enjoy walking while on vacation, the Florida Keys Overseas Heritage Trail is accessible to many points along your sailing route. 

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Sailing Catamaran "Sirius"

Ocean Sailing Inc.

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Experience the exciting world of sailing with fresh breezes and delightful sunsets on the tropical waters of the Florida Keys aboard the 24 passenger 36ft sailing catamaran

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Sunset Cruise

Approximately two hours, $40. per person plus tax

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Departing Safe Harbor Marathon Marina and Lazy Days Restaurant South

11th Street Ocean Marathon, FL.

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For information and reservations call today (305) 304-2982

Discover and enjoy the luxury of personalized attention as you and the entire family experience a safe and relaxing sail aboard the sailing catamaran "Sirius"

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boating guide

In addition to the best offers we have for boat and yacht charters in Key West, FL, see also options available for rent in these nearby locations:

  • 25 boat rentals in Key West, FL
  • 25 boat rentals in Stock Island, FL
  • 25 boat rentals in Cudjoe Key, FL
  • 25 boat rentals in Summerland Key, FL
  • 25 boat rentals in Little Torch Key, FL
  • 25 boat rentals in Big Pine Key, FL
  • 10 boat rentals in Marathon, FL
  • 10 boat rentals in Key Colony Beach, FL
  • 10 boat rentals in Duck Key, FL

Catamaran Charters in Key West, FL | Sailo Boat Rental

Looking for a catamaran charter in Key West? Boat rental in Key West, Florida   is always a great way to enjoy sailing trip experience in Florida. Choose your perfect catamaran charter with Sailo and set a course for adventure! When you rent a boat in Key West, you can choose your own itinerary and explore at your leisure. Want to relax on deck? Prefer to do some fishing? Or maybe you just want to escape the crowds? Find your ideal yacht rental in Key West with Sailo.

Our finest collection of catamaran charters in Key West, FL

Key West, FL is a well-known boating destination in the US, perfect for a memorable experience on a Sailo boat. The catamaran rentals are popular for both locals and tourists and a great choice if you want to spend some quality time with your family or friends. 7 charters are currently available with or without captain, lined up in the Key West’s marinas, waiting for their guests. Rent a private catamaran in Key West with Sailo: it’s easy, quick, secured and the best choice for a fun experience in the waters of Florida.

How to find the ideal catamaran charter in Key West, Florida?

Sailo has the most advanced filters to help you find the perfect boat rental for an amazing experience on the water in Key West, FL. Start your search by choosing your start trip date, duration and number of guests. For a great day trip with your family or friends, you have the option to select 2, 4 hours or full day rentals. Depending on your preferences and budget, you may narrow your results by boat type and price range. The 'crew' filter allows you to check the boat rentals with the captain included in the price, skipper optional (paid as extra) or bareboats that you’ll captain yourself (boating resume required). Once you have laid your eyes on a boat you like in Florida, click on it to read the description, reviews and see more pics. We also recommend using our direct 'Message Owner' feature that allows you to start a conversation with the boat representative to ask away everything you want to know before you submit a booking request.

How much does it cost to charter a catamaran in Key West for a day?

Whether you are looking to rent a catamaran yacht in Key West for a city sightseeing tour, a romantic sunset cruise or an active day on the water with your family or friends, we're confident you’ll find the best one for you on Sailo. The average starting price to charter a yacht in Key West is $1100. You can however find excellent affordable rentals from $250 and also elegant yacht charters that can go up to $6500 (service fee and mandatory extras not included).

Can I pay in installments for my Sailo catamaran rental in Key West?

A lot of our boat owners allow payment in installments, particularly for the weekly charters. First installment is always charged at the time the booking is confirmed. To find out if a boat has an installment plan, reach out to the boat representative and ask details via 'Message Owner' before you submit the booking or check out the Payment Schedule at top of the booking page.

Guidelines to responsible yachting

If you’re looking to explore our beautiful planet, a yacht charter is a great place to start. Explore coral reefs with your snorkel, discover hidden bays and islands and generally enjoy the view of nature. Remember, that sailing motto:  'Take only photos, leave only wake'  (OK, so we paraphrased). To be a responsible sailor, remember:

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Sailing the Florida Keys: 2 week Florida Keys Sailing itinerary

By: Author Reilly Mulligan

Posted on Published: August 5, 2023  - Last updated: October 9, 2023

Categories Florida Keys

Home » Florida Keys » Sailing the Florida Keys: 2 week Florida Keys Sailing itinerary

Sailing the Florida Keys: 2 week Florida Keys Sailing itinerary

Looking for a guide to sailing the Florida Keys ? You have come to the right place! Here’s a full circumnavigation Route of the Florida Keys from an avid Florida sailor. 

The Keys are a magical place and the only place in the continental US where you will find water that is a classic crystal clear turquoise shade. You could spend months exploring the hundreds of reefs and keys. If you don’t have months to spend exploring, I have got you covered.

I’ve compiled a cohesive itinerary for your Florida Keys circumnavigation that can be done within a week, but you’ll want to have more time. I promise. I would recommend that you set aside at least two weeks for this trip, so you can stop and explore the places that stand out to you the most.

This sailing journey through the Keys begins in the Miami/ Key Biscayne area. If you don’t have your own sailboat, you can rent one from sailo.com . For this journey, a sailboat with a shoal keel or a catamaran would be the best fit, as the Florida Keys are surrounded by relatively shallow waters.

The sailboat / yacht rentals out of the Miami/ Key Biscayne area are currently ranging from $450-$2000+ a day. I would recommend doing as much provisioning as possible while in this area, as you will have a wider variety of options and a better deal on gas and diesel.

After you get your boat stocked up and ready for your trip, you can anchor or moor off of Dinner Key for the night before starting your journey.

Florida Keys Sailing Guide: A 2 week itinerary

1. sailing from dinner key to rodriguez key.

49 Nautical Miles // 8 hours of sailing

If you decide to spend the first night of your journey at Dinner Key, the city has moorings available for $29.16 a night for vessels under 40 feet.

If you opt to spend the money for the mooring ball, you will also have access to pump-out facilities, laundry, exceptionally clean bathrooms and showers, and a dinghy dock (although it is quite a distance from the mooring field). There is also a shuttle service that runs to the mooring field from 8 am-5 pm; however, it doesn’t run if there are high winds and can result in having you stuck on shore without a ride back to your home.

This spot off Dinner Key offers very little protection and is open to all directions except the east.

Once you have weighed anchor and are ready to start heading to your next destination, head southwest towards the Biscayne flats, south of Key Biscayne.

If you want to stop for the night or need to duck away from an oncoming storm, you can anchor in No Name Harbor or along the edges of the Cape Florida Channel. After passing through the Biscayne flats, keep heading east towards the Atlantic Ocean. Once you’ve bypassed all of the channel markers, turn south and start heading through the waters of the Biscayne National Park.

Keep heading south down Hawk Channel, you will soon come to an area known as Mosquito Bank. Once you are sailing through the Mosquito Bank, you will see Rodriguez Key to your southwest. There are crab pots virtually everywhere, even within the channel. Be sure to be on the lookout, if you plan on getting in after dark it is crucial that you have a reliable bright spotlight.

I recommend anchoring on the northwest side of the island, in order to get the most protection possible. You might have a little bit of trouble trying to get your anchor to set, as the bottom consists of seagrass, rock, and coral.

Keep in mind that it is illegal to anchor on coral, so be sure to find a patch of sand or seagrass to drop the hook in. For southbound travelers, this is their first taste of the crystal clear water that the Keys are known for.

On days with better visibility, you can sometimes see your anchor in 7-10 feet of water. After getting your anchor set, be sure to go to shore and do some exploring on this beautiful, untouched mangrove island.

Dinner-Key-to-Rodriguez-Key-sailing-the-florida-keys

2. Sailing from Rodriguez Key to Little Crawl Key

37.9 Nautical Miles // 6 hours of sailing

Be cautious of crab pots along this route as they are littered everywhere. You should have no issues as you’re heading south down Hawk Channel, it is a relatively well-marked channel.

Once the channel starts bearing more west, you will find yourself coming up to the south side of Tavernier Key. You can also stop here and anchor for the night on both the north and south sides of the island and it has a decent sandy bottom that provides good holding. Little Crawl Key is home to Curry Hammock State Park.

Curry Hammock State Park is the largest piece of untouched land between Key Largo and Big Pine Key. If you visit during the fall you may be lucky enough to witness the huge migration of peregrine hawks that stop on the island on their pilgrimage south. Little Crawl Key is just south of Crawl Key.

They’ve been given their names due to the large number of turtle nesting that occurs on the island, with tons of tiny hatchlings crawling to the sea every year.

There are mangrove paddling trails that you can traverse on a kayak, dinghy, or paddleboard to get an up-close and personal view of the mangroves and all of the life inside of them. There are also hiking and biking trails on land if you would like to spend some time with solid ground under your feet. 

Rodriguez-Key-to-Little-Crawl-Key

3. Cruising from Little Crawl Key to Newfound Harbor Key

28.8 Nautical Miles // 4.5 Hours of Sailing

Before heading west out of Hawk Channel, be sure to stop at Looe Key Reef to do some amazing snorkeling and diving. There are tons of mooring balls surrounding the island on a first come first serve basis, be sure not to drop the hook on any reef or coral, as it is illegal.

If the mooring balls are all taken and you must anchor, be sure to find a nice patch of sand to drop the hook in.  You will find some of the best snorkeling and diving in the Florida Keys at the reef off Looe Key. While swimming around the reef you may come across some goliath groupers, spotted eagle rays, barracudas, or even a black-tip reef shark.

If you have extremely placid weather, you may be able to spend the whole night at Looe Key Reef. However, if you have any type of wind or swell, I would recommend heading a bit further inland for the night. Leaving the reef, head west-northwest towards Big Pine Key.

There is a slightly shallow area just north of Munison Key where you should keep an eye on your depth finder. You will find a ½ square mile of reef just off the coast of Palm Island that hosts an amazing diversity of coral, including fan coral, brain coral, boulder coral, and star coral.

Diving, while there is a northwest wind blowing, will provide you with the best conditions for good visibility.

Little-Crawl-Key-to-Newfound-Harbor-Key-sailing-the-florida-keys

4. Cruising from Looe Key to Key West

25.3 Nautical Miles // 4 Hours of Sailing

As you are approaching Key West ; your senses may start to overwhelm you. It is one of the best places to go sailing in the Florida Keys.

You will be able to hear the music and people laughing from the downtown area, smell the burgers cooking on the grill, smell the deckhands cleaning fish on the docks while joking with their crewmates, and hear an almost constant buzzing of motors and jetskis all around the island.

You can anchor in the northwest inlet of Fleming Key, and dinghy into downtown from there. You will still have a little bit of traffic buzzing around you, which is virtually impossible to avoid in such close proximity to Key West. You can also anchor on the Northeast side of Wisteria Island, which is a good option as well.

However, a few people have reported that there is a sizable amount of derelict boats off of Wisteria Island that tend to drag if there is any weather at all. It is also a considerable distance from the dinghy docks on Key West. If you decide to leave your tender at the dinghy dock, it costs $8 a day. I would still recommend locking up your belongings to make sure that everything is where you left it when you return.

Once you get onshore in Key West, the activities available are essentially endless. There is something to do for the whole family. If you are a literary lover, you can stop at the Hemingway Home and Museum and meet the six-toed cats that live on the grounds.

You can also get a tour and see where Hemingway spent his nights writing his multiple masterpieces. The pool on the premises was constructed in 1938, and is gargantuan in size, especially for this era. It was the only pool within 500 miles of Key West when it was constructed. Entrance to the Hemingway Home costs $18/day for adults, $7 for children between 6-12 years old, or free for children 5 and under. Entrance into the home also gives you access to a 20-30 minute guided tour.

If you would like to get a little more in-depth view of the life of Ernest Hemingway, you can grab dinner and a drink at Sloppy Joe’s Bar, one of Hemingway’s favorite hang-outs.

Looe-Key-to-Key-West

If you would like to see a more colorful side of Key West, you can visit Nancy Forrester’s Secret Garden. Nancy Forrester’s Secret Garden is a parrot sanctuary that homes multiple endangered species of macaws and parrots.

Entrance to the sanctuary costs $10 for adults and $5 for children between the ages of 5 and 11 years old.

A visit to Key West is not complete until you’ve got a photo taken in front of the Southernmost Point in the Continental US, a classic must-see stop that is free to visit. From this point, it is only 90 miles to Cuba.

Duval Street runs right through the middle of Key West, oriented to run north and south. There are tons of little shops and cafes to stop and poke in and grab refreshments when necessary. If you find yourself on the north side of Duval Street, you will come across Mallory Square.

Mallory Square is known for its magnificent view of the sunset, and the countless buskers and street performers earning their living everywhere that you look. If you have a hankering for something sweet, be sure to stop at Kermit’s Key West Key Lime Shoppe for a frozen dark chocolate-covered piece of Key Lime Pie .

If you want to be blown away by the impressive size of the marine wildlife that Key West has to offer, take a trip over to Stock Island and visit Robbie’s of Key West Marina. There is a $2.50 entrance fee to go out on the dock and $4 more for a bucket full of fish to feed the tarpon. You will be able to see your hand and wrist get completely swallowed by a tarpon before it takes its treats and releases your appendages.

things to do in key west

5. Key West to Dry Tortugas

64 Nautical Miles // 10 Hours of Sailing

Dry Tortugas National Park is a 100-square-mile park. It is a bird watcher’s paradise. It is one of the only places in the continental US where you can find endangered sooty terns nesting.

It is also home to one of the only known nesting colonies of frigate birds. There have been over 300 species of birds identified within its grounds. Fort Jefferson, an octagonal fort, proudly dominates Garden Key. The construction for it began in 1845. It was meant to be a military installment for US ships to patrol the Gulf of Mexico Construction was never completed and the fort was never armed, but it still sits on Garden Key, the second largest key in all of the Dry Tortugas.

Garden Key is also home to the visitors center, parks headquarters, and campgrounds. Entrance to the park costs $15 a person, excluding people under the age of 16, and is paid through a self-service fee area on the main dock at Garden Key.

here are no trash receptacles on the island so you need to “pack in and pack out” everything that you bring. Be sure to respect your neighbors and mother nature, and remember that littering is illegal. There are also no lifeguards on duty so swimming is at your own risk. It is encouraged to always use the buddy system while swimming or snorkeling

Keep in mind that it is illegal to molest, stand or sit on coral, as it does a considerable amount of damage to the ecosystem.

Anchoring on the southeast side of Fort Jefferson typically allows you the best protection. Once you get the hook set, you will find yourself in a remote tropical paradise. The Dry Tortugas National Park is only accessible by seaplane, ferry, or private boat.

The Dry Tortugas has some of the best fishing that you will ever have the pleasure of experiencing. People with their own boats are required to get a boating permit for each vessel in order to be allowed to fish. These permits are free and can be picked up at the Garden Key Dock House.

You will need to get a boating permit for any type of vessel including kayaks, paddle boards, or dinghies. You will also need your Florida saltwater fishing license . Lobstering and spearfishing are both prohibited within the park. “J” hooks are not permitted to be used within the park, but “circle” hooks are acceptable.

If you’re lucky, you’ll be able to catch some of the amazing gamefish that call the Dry Tortugas their home such as amberjacks, bluefin tunas, blackfin tunas, wahoos, kingfish, black grouper, red grouper, swordfish, sailfish, and permits. The species of fish that you pull up will be dependent on the time of year that you go.

There are also at least five turtle species present in the park including Loggerheads, Green Turtles, Kemp’s Ridley, Hawksbill, and Leatherbacks. President Franklin D. Roosevelt designated the fort a national monument. Now, you cannot remove any seashells, sand, rocks, coral, or glass from the national park.

things-to-do-in-Dry-Tortugas.

If you don’t feel up to making the entire 64-mile trip, you can stop about halfway in between Key West and the Dry Tortugas at the Marquesas Keys, turning the voyage into a slightly more manageable two-day trip.

The Marquesas Keys, not to be confused with the Marquesas Islands found in French Polynesia, are located about twenty miles west of Key West. It is sometimes referred to as “Button Island” due to its round shape. It was known to have been used for military target practice as recently as the 1980s.

The Marquesas are four miles in diameter, and the lagoon located in the center is known as Mooney Harbor. After leaving Marquesas Keys, it is a 36-mile distance to the Dry Tortugas.

Dry-Tortugas

The next section of this sailing route through the Keys is through the Inner Passage, on the northwest side of the Keys in the Florida Bay, rather than the Atlantic Ocean side.

his region in the Florida Keys is rather shallow, and I wouldn’t recommend attempting the journey without a functioning transducer on board. Also, if your boat draws more than five feet, you may want to reconsider and complete the trip through Hawk Channel, on the Atlantic Ocean side.

Key-West-to-Dry-Tortugas-sailing-trip

6. Dry Tortugas to Snipe Point

64.2 Nautical Miles // 10 Hours of Sailing

After visiting Key West and the Dry Tortugas, you may want to get away from the tourists a bit and hang out where the locals like to hang out. I would recommend going to Snipe Point on a weekday because the sandbar can become one giant party on the weekend.

Snipe Point is within the Great White Heron National Wildlife Refuge, which was established in 1938 as a refuge for migratory birds, great white herons, and other tropical wildlife.

This area is commonly referred to as “the backcountry” by locals. Tons of turtles use this beach as a nesting area, so be sure to keep a lookout for nesting spots, and keep your lights to a minimum at night. Great White Heron National Wildlife Reserve consists of 1,000’s acres of untouched shallow, crystal clear waters and mangrove islands.

There are no pets permitted on shore. Be sure to keep your eye out for crab pots as they are littered everywhere around the island and channel.

Dry-Tortugas-to-Snipe-Point

7. Snipe Point to Fat Deer Key

41 Nautical Miles  // 6.5 Hours of Sailing

Fat Deer Key is located just north of Marathon and south of Long Point Key. It is another of our favorite places for Sailing in the Florida Keys.  On the Atlantic side of the island, you will find Coco Plum Beach, with its pristine white powdery sand. This is a great place to hang out if you wish to spend the day cooling down a little bit.

Curry Hammock State Park is located on Fat Deer Key, and within this park you will find the Curry Hammock State Park Nature Trail. Once entering the park, travel west for one mile to find the mouth of the hiking trail. You can find parking on either side of the road.

The hammock that shadows over you gives you a little bit of relief from the hot Florida sun. This state park is home to the largest thicket of Florida thatch palms in the continental US.

Fat Deer Key is just north of Marathon. Marathon is a well established city, and you will find everything you need to reprovision and top off your gas and/or diesel tanks.

Once on shore, there are a multitude of marina and dive shops that you can check out. Some of them include: Captain Hooks Marina and Dive Center and Driftwood Marina and Storage. If you are hungry for some delicious, fresh seafood be sure to stop in at SS Wreck and Galley Grill or the Island Fish Company. You can also check out Florida Keys Aquarium Encounters while exploring Marathon.

Snipe Point to Fat Deer Key

8. Fat Deer Key to Butternut Key

45.5 Nautical Miles // 7 Hours of Sailing the Keys

Butternut Key is located in Florida Bay, the body of water between the Florida Keys and the southern tip of Florida, east of the Gulf of Mexico.

Butternut Key is off the southwest coast of Key Largo. Technically, it is considered to be a part of the Everglades National Park . The maximum stay that is permitted is 14 days. There is a poll and troll zone within 300 feet of the islands, meaning that motors are not permitted.

It is easiest to approach the island from the southwest, off of the Intracoastal Waterway. You will have a 6-7 foot depth at low tide. Just like every other anchorage on the west side of the Keys, be sure to keep an eye on your depth sounder. The bottom is fine sand and soft mud and provides excellent holding. The anchorage is the most comfortable if it is blowing out of the North or East.

You’ll have a fantastic view of the sunset, as this spot is completely open to the West. This untouched, serene, remote tropical paradise inspires everyone who has the pleasure of laying eyes on it, including legendary artist Clyde Butcher. He traveled to Butternut Key in 1997 to preserve her beauty in a photograph forever.

Fat Deer Key to Butternut Key

9. Butternut Key to Dinner Key

49 Nautical Miles // 7 Hours and 45 Minutes of Sailing

When you depart from Butternut Key, head southeast toward the Atlantic Ocean, and then start heading up north once you reach Key Largo. Heading west you are first going to sail north through Baker’s Cut and enter into Buttonwood Sound.

Keep heading northeast through Buttonwood Sound, until you reach Grouper Creek. Again, keep your eyes on your depth sounder to make sure you don’t run aground. Also, keep a diligent eye out for crab pots that cover the waterways through here. After passing through Grouper Creek, you will spit out to the east into Tarpon Basin. As you continue heading north up the Intracoastal Waterway, you will soon enter Dusenbury Creek.

For this portion of the sailing route, it is crucial that you have a functioning engine onboard, as these voyages are nearly impossible without one. After exiting Dusenbury Creek, you will find yourself in a large bay, known as Blackwater Sound.

Continue heading northeast until you come to the mouth of Jewfish Creek. Jewfish Creek will bring you to Barnes Sound, then Card Sound, and then finally Biscayne Bay, inside of the Biscayne National Park. You will be able to anchor back at Dinner Key or find a slip in a marina to treat yourself after your jam-packed voyage.

Butternut Key to Dinner Key

Final Thoughts Before you set sail on your Yacht

If you plan to use our guide to Sailing the Florida Keys, we would love to hear from you so leave us a comment below.

Want more great Florida sailing routes? be sure to check out the Best Places to go Sailing in Florida !

Author: Reilly Mulligan is a sailing enthusiast from Florida who has spent her life sailing and exploring the Sunshine State.

Reilly Mulligan

Reilly is a sailing enthusiast from Florida who has spent her life sailing and exploring the Sunshine State. A native Floridian born who raised in St. Petersburg, Florida, Reilly has spent her whole life going on interesting, off-the-beaten-path trips around the state of Florida and has a plethora of information and experiences to share! While she is not sailing her boat around the Sunshine State she is sharing her experience traveling around the State with the readers of Florida Vacationers!

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READY. SET. SAIL THE FLORIDA KEYS

At the end of a 110-mile-long chain of islands, stretched like a string of pearls across a Caribbean blue sea lies charmed Key West, it is here you will find Florida Yachts Charters. We are a boutique yacht charter company that specializes in Bareboat and Crewed Charter, ASA Sailing Instruction and Yacht Management. Experience the best of sailing the Florida Keys with a well maintained fleet of yachts, local knowledge and expertise, a warm island welcome and the personal touches of a luxury yacht charter.

Bareboat Charter

Raise the sails or take the throttle. With a bareboat charter i f you have the experience, then enjoy the freedom of captaining your own yacht on your own Florida Keys adventure. Explore our fleet of sailing monohulls, catamarans and power yachts.

Captained Charter

Sit back, relax, and let the professionals do all the work. Charter the yacht of your choice and connect with one of our experienced crew for your carefree sailing vacation in the Florida Keys. Want a full-service chef, we can help with that too!

Learn to Sail

Let us show you the ropes. Do you dream of owning or bareboat chartering your own sailing yacht one day? We are an accredited ASA Sailing School offering fully private courses for high quality one on one time with your instructor. Customize your itinerary and turn your Florida Keys sailing vacation into a great educational opportunity for you and your family.

Yacht Management

If you are dreaming of enjoying the luxury of keeping your yacht in paradise then join our curated fleet of well maintained charter yachts. We will be happy to consult with you about our yacht management options in the Florida Keys.

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catamaran sailing florida keys

catamaran sailing florida keys

Top 7 Best Florida Keys Sailing Tips

catamaran sailing florida keys

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Sailing is a great way to increase your alertness and has many emotional and physical health benefits . Whether you’re new to sailing or are a seasoned sailor, I have gathered some awesome information you need to sail the Florida Keys.  

catamaran sailing florida keys

Table of Contents

1. The Off-Peak Season Can Save Lots of Money

From chartering a boat to finding places to eat, everything is more expensive during peak season. While this isn’t surprising as it follows the basic law of supply and demand, it can certainly work in your favor. Knowing the best time to sail the Florida Keys will ensure you get the best deals everywhere you go. 

The off-peak season for the Florida Keys is from March through November. During this time, you can expect to see many deals on places to stay, boats to charter, and fun things you want to do on the trip. 

If you plan to stay in hotels around the Keys, taking the trip during the off-season will save you a lot of money. Budgeting is an important part of any trip, and saving enough money can mean more trips in the future. So, make sure you consider sailing during the off-peak season.

catamaran sailing florida keys

2. Charter a Boat To Reach More Destinations

While sailing the Florida Keys, you may consider stopping along the way to stay at hotels. This is a valid choice, but it can really slow you down. If you want to see as much of the Florida Keys as possible, consider chartering a boat. 

This way, you can have everything you need right there. You can get a boat that comes with lodging, a kitchen, a crew, and even a chef to cook for your group. Without worrying about where to eat and sleep, you can spend a lot more time deciding on the cool places to visit instead. 

While crew members and larger charter boats aren’t cheap, always compare the cost to staying at hotels throughout the Florida Keys. You may save some money by chartering your own boat rather than paying for places to stay. You can also save money by making your own food on the boat rather than consistently eating out. 

Chartering a boat during your visit gives you much more control over all the aspects of your trip. 

catamaran sailing florida keys

3. The Florida Loop Route

One of the most important tips for sailing is to always know where you’re going. This will prevent you from getting lost or running into trouble.

Sailing is a fun and relaxing activity, but it can be dangerous if you don’t know where you are or where you’re going at all times. 

If you’re planning on sailing the Florida Loop , it’s especially crucial to keep your bearings. This route ( also known as Smuggler’s Run ) travels from the St. Lucie canal, south past Miami, and then loops around Key West.  

From that point, it makes a northward turn, toward Cape Coral and the mouth of the Caloosahatchee River. It then follows the river into the Caloosahatchee Canal and through to Florida’s east coast via the Mayaka Cut.

That said, most folks follow this route in a counter-clockwise direction , as the Gulf Stream current pushing against the bottom portion of Florida (and the Florida Keys) moves eastward. Fighting against this current by starting your journey near the Mayak Cut (instead of traveling south out the Caloosahatchee River) can be challenging.

If you’re not prepared to tackle the Florida Loop, either with navigation tools or an experienced guide, you can quickly end up drifting out to sea while attempting to make your way south to Key West. For that reason, it’s crucial to always stay aware of your current location, vessel direction, and sailing speed.

catamaran sailing florida keys

4. Make Sure You Have Plenty of Provisions

An important part of sailing, no matter where you’re going, is to have plenty of supplies and provisions to ensure your safety and well-being during the trip. 

A good rule of thumb for sailing is to bring 1.5 to 2 times the amount of provisions that you’ll need for the trip to be safe . Whatever the amount you choose, it’s best to at least bring enough food for a few extra days. 

Weather can be unpredictable, and storms can throw your boat off course. There may also need to be times when you could be moving, but you aren’t. When sailing, there are plenty of things that can keep you off schedule. 

That said, don’t worry that you won’t be able to find stops along the way to restock on provisions. The Oceanside Marina in Key West, for example, is a top-notch place to stop and grab some snacks and extra gallons of water . In fact, this marina is part of the brilliantly named Stock Island.

While you might not find many provisions at the marina, Lacurva Groceries is only about a five-minute car ride away. If you’d rather opt out of rideshare services, you can walk there in about 20 minutes! 

Additionally, the Tavernier Creek Marina (in Plantation Key) is only about a mile away from the nearest Winn-Dixie grocery store. So, if you find yourself further up along the Florida Keys in need of snacks or drinks, you can always make a quick stop here and stock up on goodies

5. Keep An Eye Out for Debris

Another important rule for sailing is to ensure that you watch out for debris. You can find debris on the water from just about anything, but it’s especially common after a hurricane.

Hurricanes tend to cause a lot of debris from boats, trees, and even homes to be a nuisance when traveling on the water. 

Additionally, the Florida Keys are home to some of the state’s oldest fisheries and fishing ports. As such, decades’ worth of washed-away fishing gear may be floating around near the shorelines, potentially causing problems for you and your vessel.

Debris may seem like it’s not a big deal, but it can be dangerous when sailing. Your propellers can get entangled in fishing net and become hard to get free of. Hard debris can also damage the hull, props, or rudders costing you a lot of money or even impairing the boat enough to make it unsafe. For that reason, you’ll want to watch out for it and avoid it if you can. 

catamaran sailing florida keys

6. Avoid Hurricane Season

We already discussed how beneficial the off-peak season could be for your bank account, but there’s another factor to consider.

In the Florida Keys, hurricane season is between June and November . You can save even more money visiting during this time, but that’s because there’s a greater risk of hurricanes. 

Hurricane season slows down visitors, but it certainly doesn’t stop everyone. From destination weddings to brave sailors, the Florida Keys is never empty. But hurricanes are dangerous, especially for sailors. So, let’s talk about why it’s best to avoid hurricane season as a sailor. 

There’s never a guarantee that your boat will survive the high winds and rough waters that a hurricane can bring. So, it’s best to avoid them altogether if possible. Unfortunately, they’re difficult to track accurately. So, an area that may seem safe now could be in danger if the hurricane changes course. 

So, when sailing the Florida Keys, avoid hurricane season if possible. While it’s cheaper than other times of the year, it’s also a lot more dangerous. So, keep yourself, your boat, and your loved ones safe by planning your trip around this season. 

catamaran sailing florida keys

7. Stop for Some Key Lime Pie

If it’s your first time visiting the Florida Keys, you’re in for a treat. While the exact origin is unknown, key lime pie is a dessert that has truly taken over the area. Offering some of the best options for dessert, the Florida Keys is the best place to get a key lime pie.  

Key limes are grown only in places that never get below freezing. The tropical temperatures of the Florida Keys help grow the most flavorful key limes. So, it’s no surprise that you can find it all over the place here. 

Try a few different places and see which one has your favorite recipe, or make it a tradition to try a new place every time you go. However you do it, make sure you try some while you’re in the Florida Keys. Whenever you plan your trip, make sure to stop for some fresh, flavorful key lime pie along the way. 

Frequently Asked Questions 

If you still have some unanswered questions about sailing the Florida Keys, then we have just what you need. Read on as we answer some of your most common questions. 

Can You Sail Around the Florida Keys?

You can sail around the Florida Keys. Sailing from Miami to Key West takes around 15 to 26 hours. This is a very popular route and offers plenty of amazing stops.

You may be a little more comfortable if you have your own boat, but you can rent or charter your own without much struggle whenever you plan to visit.

When you do sail the Florida Keys, you can do so with or without stopping. The choice is yours. If you’d like to sail all the way around, feel free. But there are plenty of interesting places to stop along the way if you want to add some more experiences to your vacation. 

When Can You Sail the Florida Keys?

You can sail the Florida Keys year-round. Just be careful during hurricane season (June 1st to November 30th) as the water can quickly become a dangerous place when a hurricane approaches. 

While it may seem strange to have something available to you all year round, that’s the case with sailing the Florida Keys. It may be best to avoid sailing during hurricane season, but it’s certainly not forbidden during these months. As long as a sailor feels experienced enough and knows when to sail toward safe harbor, they can sail right through hurricane season if they want to. 

How Long Does It Take To Sail From Miami to Key West?

It’ll take you a little over a day to sail from Miami to Key West directly without stopping (15 to 26 hours). There are plenty of places to stop along the way. So, plan for a longer trip for anything you may want to do along the way. 

This day-long trip doesn’t leave much time for sightseeing or stops for food. So, if you want to stop for longer or make some extra stops, plan for a longer trip. If you need some help planning your Miami to Key West sailing itinerary, there are plenty of resources out there to help. 

For your trip to Key West from Miami, try sending me an email here . I have a list of some of the most popular destinations along the way that will allow you to see some popular sights as you make your way to Key West. 

Planning trips like this one are vital because there are many spots between Miami and Key West that can be dangerous or forbidden depending on the time of day or part of the season. Keep an eye out for markers that indicate an area is off-limits, and remember to check with local areas for parts to avoid during low tide. 

Final Thoughts

Sailing the Florida Keys is a popular vacation choice for people all over. Follow my tips to ensure you have a safe and fun trip, whether it’s your first time sailing or you’ve done it before. 

Whatever you’re planning to do during your visit to the Florida Keys, be aware of hurricane season, good food spots, and pay attention to your surroundings at all times. Get the planning out of the way ahead of time, so you can relax and enjoy your trip. 

Here are Some of My Favorite Catamaran Cruising Resources

Thank you for reading this article. I hope you found it helpful as you hopefully start your sailing adventures. Here are some resources that I use as a sailor that I hope you’ll also find helpful. These are affiliate links, so if you do decide to use any of them, I’ll earn a commission. But in all honesty, these are the exact things that I use and recommend to everyone, even my own family. Sailboats: If you’re looking for the best boat to suit your needs, I would recommend a catamaran. If you’re interested, I can show you the differences between catamarans and other types of sailboats .

Books:  For getting started, I really like  Cruising catamarans made easy . It is actually a textbook from the American sailing association; it is used to get a cruising catamaran certification. There are some other great books, and I have compiled a list of books about cruising catamarans that you will find useful.

Communication:  Being out on adventures, whether it be sailing or climbing mountains, good communications are essential to being safe. I recommend two things Google fi (incredibly simple cellular data all over the world) and Garmin inreach mini (for text and voice in remote areas without cell coverage)

Sailing courses: Online sailing courses are great for beginners starting out their sailing career; it’s an efficient way of learning the basics of navigation, throttle controls, and maritime safety. I suggest starting with two free courses from NauticEd .

To see all my most up-to-date recommendations,  check out this resource  that I made for you!

Owner of CatamaranFreedom.com. A minimalist that has lived in a caravan in Sweden, 35ft Monohull in the Bahamas, and right now in his self-built Van. He just started the next adventure, to circumnavigate the world on a Catamaran!

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Florida Keys Sailing

catamaran sailing florida keys

The Spanish first found the Keys during Ponce de Leon's expedition in 1513. They mapped and named the Keys principally as an aid to their ships, which, full of gold and silver, used the Florida Straits to go from the New World back to the Old. The first settlement was at Key West, in 1882, a little more than two decades before Florida became a state. The other Keys pretty much stayed deserted until 1874, when the government surveyed them. After the survey, the government plotted land for businesses and homes. The early homes were primitive. They were built from the local beaches, made of wood and other materials washed up from shipwrecks. In 1912 Henry Flagler built a railroad to Key West. This greatly increased human settlement of the Keys. The railroad was destroyed by a hurricane in 1935, but in 1938 the longest over-water road in the world was built on the railroad's foundation. It includes 42 bridges--one that is seven miles long! This opened the Florida Keys up to a growing tourist trade.

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A Guide to Sailing in the Florida Keys

Known for coral islands and sandy picnics, the Florida Keys are an incredible sailing destination

There are over 880 reasons why the Florida Keys are the best yacht charter destination in America. This endless chain of coral islands wiggles from Miami to Key West in a sandy necklace licked by the sun. Only 30 of the islands are populated – mainly by lucky park rangers and oyster shack shuckers. Anchor off the hundreds of other Florida Keys for dolphin spotting, mangrove kayaking, desert island picnics and whirlpool-warm seas. Access? Solely by sea.

For a seamless day sailing the Florida Keys.

What to see and do in the Florida Keys

Heading south from Miami, Key Largo is first in line. This Florida Key hosts America’s first undersea sanctuary – the John Pennekamp Coral Reef State Park. Step off your yacht with snorkels, scuba tanks, or a glass-bottomed kayak. Finding Nemo? He’s right here, along with yellow snappers posing for selfies and lobsters peeking out from coral reefs.

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Shhh. The Florida Keys extend just under another 100km (62mi) west from Key West in the form of the Dry Tortugas. This little-known collection of coral islets is protected within a National Park that’s 99% water. The archipelago is linked by an irregular ferry service and hosts a single rustic campsite, making a chartered yacht the ultimate way to arrive. From the deck, spot loggerhead turtles, bottlenose dolphins and magnificent frigatebirds.

catamaran sailing florida keys

Best mooring locations in the Florida Keys

Key West’s line of petite marinas is sheltered on the northern side of the island – a stroll away from dozens of oyster shacks and lobster houses. Conch Harbor Marina offers free bikes, document printing and hammocks to sailors who tie-up – plus iced beers, two restaurants and a fishing store. Call ahead or contact them on open VHF Channel 16. Paradise is a tie-up to a mooring buoy off Looe Key – while the island is a National Marine Sanctuary where sea life congregates in droves. Leap over the side to see parrotfish, butterflyfish and jacks. As with all coral reefs, look but don’t touch.

Sailboats docked at the Conch Harbor Marina in Key West in the Florida Keys

Where to eat and drink in the Florida Keys

The sustainable larder of the Florida Keys is stocked with stone crabs, mahi-mahi and lionfish – where your menu should include shrimp tacos, Cuban pork and conch fritters. All crowned by a calorific wedge of key lime pie. No establishment on Key West can be considered fancy – Red Shoe Island Bistro simply gathers top drawer ingredients then serves them on the half shell, au beurre, or simply grilled. Harpoon Harry’s is as unabashed as its name – Join salty seadogs for a lobster po’boy or a seafood platter with the works. Pair with Bigger Boat White, a malty pilsner beer brewed in the Waterfront Brewery in Key West.

Harpoon Harry’s Restaurant and Bar in the Florida Keys

Best charter options in the Florida Keys

Sailing a motorized catamaran is a cinch . You can cruise the Florida Keys – with or without a skipper – with horsepower under the bonnet and not a single sail to worry about. Hire a vessel with Dream Yacht Charter , from skippered charters to bareboat fleets, let the captain do the work unless you’re a sailor.

An elevated view of sailing ships in the Florida Keys

Where to get groceries in the Florida Keys

New Market is the marina neighborhood store for pickles and mayonnaise to accompany your lunch on Picnic Island – yes, there’s a clue with that name. The Sunbeam Grocery, a few blocks east of Key West’s marina strip, is bigger and less expensive. Stock up on all-American snacks, international beers and Taittinger Champagne to bring out your inner James Bond.

Key annual sailing events in the Florida Keys

The Buccaneer Blast kicks off from Key Largo’s Upper Keys Sailing Club each February. The two-day race sees scores of younger sailors compete in Lasters, Optimists and Open Skiffs.

Climate and weather in the Florida Keys

As a yacht charter destination, Florida is fabulous for up to 10 months per year. Easterly winds promise 10-knot breezes through spring and autumn, rising to 15-knots in winter. Best of all, the reefs that surround the “American Caribbean” ward off choppy seas. Sunny? The Florida Keys and Miami Beach are the only places in the continental United States that have never recorded a frost. Winter highs average 25°C (76°F) while sea breezes stop summers from scorching. The only poor period for sailors is between late August and early October when sultry squalls and the occasional hurricane drift in. Sailors are advised to keep a keen eye on tides, too.

Sailing boats sit on South Beach in the Florida Keys

How to get to the Florida Keys

Most travelers fly into Miami International airport. The Florida Keys start a one-hour drive south at Key Largo. From here, it’s a sun-drenched 148km (92mi) drive down Highway 1 to Key West. Here, minor airport Key West International welcomes smaller jets from North American cities, including Chicago and New York.

Set sail around the Florida Keys.

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Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

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catamaran sailing florida keys

See & Do

How to spend days island hopping in the florida keys.

catamaran sailing florida keys

Moor Up at These Alternative Marinas in the Florida Keys to Avoid the Crowds

catamaran sailing florida keys

Places to Stay

The best vacation rentals to book in the florida keys.

catamaran sailing florida keys

The Best Beach Hotels to Book in the Florida Keys

catamaran sailing florida keys

The Best Beach Hotels to Book in Key West, Florida

catamaran sailing florida keys

Secret Keys: Hidden Attractions in Florida’s Tropical Archipelago

catamaran sailing florida keys

Key Largo to Key West: Island Hopping Like a Local in the Florida Keys

catamaran sailing florida keys

The Best Hotels to Book in the Florida Keys

catamaran sailing florida keys

The Best Boutique Hotels to Book in the Florida Keys

Winter sale offers on our trips, incredible savings.

catamaran sailing florida keys

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Sail Your Dreams with the Family-Owned Catamaran Charter Company

Are you looking for the best option for a 4day sailing adventure in the Florida Keys?  Sailing The Space Between is a family run boat charter in Fort Lauderdale, where all your sailing needs will be taken care of. We will ensure that you experience an amazing sailing adventure with comfort and care. As a local business, we can give you an experienced and unique escapade on a Key West Catamaran trip.  We also provide Bahamas catamaran charters . 

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Our only motive is to provide you the perfect experience for your dream vacation with catamaran rental in Florida. Come join us on a trip to the beautiful waters of Florida.

4day Sailing Adventure in Florida Keys

The best way to experience the waves of tropical waters is through a Florida Keys boat charter excursion. We have the best offers and deals for romantic gateways, adventures with friends, family vacations (14 and older please), or anyone looking for fun and adventurous experiences.

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All these options are offered at very budget-friendly prices and are the best available options for your group. If you want to know more about our services, you can get the idea through our reviews from our loving clients. We specialize in providing our guests with additional fun activities. We will provide the ideal options for you along with the options of multiple activities, delicious meals, and some serene relaxation throughout your trip. We promise you the best sailing adventures in the Florida Keys.

What Are the Activities You Can Enjoy During the Trip with Sailtsb?

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Our main motive is to provide our passengers with multiple activities, making their 4 day sailing trip to the Florida Keys more memorable. We have the list of options available throughout the day:

Paddle boarding

Sub wing (underwater flying)

Snorkelling

Island excursions

Movie nights

Dinghy adventures

If you want to go on an unforgettable sailing adventure, experience the world from a new vantage point,  swim and snorkel in the largest underwater national park, John Pennycamp, and relax with the wind in your hair, we are just a call or an email away.  The captain and crew on The Space Between are thriving to make your 4-day sailing trip to the Florida Keys one of your best life experiences.

The top 3 adventures in The Florida Keys & Key West

Dive or snorkel colourful coral reefs, kayak in subtropical mangroves and pedal along winding trails in this southern oasis full of outstanding outdoor pursuits.

catamaran sailing florida keys

A 125-mile-long archipelago at the southernmost tip of the US, the Florida Keys are made up of around 1,700 laid-back islands. Stretching like a string of pearls across the teal waters of the Gulf of Mexico, the Keys are best known for sandy beaches and bohemian culture. Beyond sun-worshipping and sipping rum runners (the area’s signature cocktail), there are also boundless activities for outdoor enthusiasts keen to explore this palm-fringed paradise. From snorkelling and sailing to biking and kayaking, the Keys offer a multitude of fun ways to inject adventure into a classic Florida holiday.

Snorkelling & diving in coral gardens

With a wealth of coral-lined islands rich in marine life, the Keys are an ideal spot to sink into balmy waters and discover delicate reef systems. Just off Key Largo lies the John Pennekamp Coral Reef State Park — the first underwater park in the US. Glide through clear waters and explore vivid coral gardens teeming with aquatic life. With 48,000 acres of protected ocean to explore, you’ll find a rich ecosystem of tropical fish, sea turtles, lobsters and fierce-looking barracudas that call this diverse region home. Book a PADI scuba dive tour to get up close and personal with Christ of the Abyss — a towering bronze sculpture of Jesus below the surface of the water.

catamaran sailing florida keys

Kayaking through the mangroves

Grab a paddle and venture into the ethereal mangroves of Key West — a dense labyrinth of jungly tunnels and crystalline creeks. Guided kayak tours take you deep into this watery haven, where you’ll paddle through narrow passages shaded by the jade-green mangrove canopy. Wait until the sun sinks below the horizon and take a guided night kayak tour for the chance to see nocturnal marine life such as manatees emerging in the fading light. Family-owned tour operator Night Kayak Key West offers an evening excursion through the mangroves, where you’ll paddle a glass-bottomed kayak with LED lights illuminating the world below.

catamaran sailing florida keys

Biking the Overseas Heritage Trail

Discover the Keys on two wheels by cycling over 90 miles of paved roads on the expanding Overseas Heritage Trail , which traces the historic Overseas Railroad. With its ultimate aim of connecting Key Largo to Key West, this multi-use and largely car-free trail is perfect for those wanting to explore this scenic region under their own steam. Cycle over former rail bridges, traverse tree-lined beach tracks and glide along beside turquoise waters. Key Largo Bike and Adventure Tours offers rentals and self-guided bike tours where you can set your own pace and distance, with planned routes, luggage delivery and bike pick-up in Key West.

Related Topics

  • ADVENTURE TRAVEL
  • UNDERWATER ADVENTURE
  • TRAVEL AND ADVENTURE

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IMAGES

  1. Explore & Sail The Florida Keys

    catamaran sailing florida keys

  2. Key West Catamaran Sail and Snorkel

    catamaran sailing florida keys

  3. Sailing The Space Between Promo: Catamaran Charter in S Florida, Keys

    catamaran sailing florida keys

  4. Champagne Sunset Sailing on a Catamaran in Key West

    catamaran sailing florida keys

  5. Crewed Sailing Catamaran Charter

    catamaran sailing florida keys

  6. Champagne Sunset Sailing on a Catamaran in Key West

    catamaran sailing florida keys

VIDEO

  1. Swimming under the boat

  2. Sailing the Florida Keys in Hobie

  3. Downwind Sailing Florida Keys Sunset

  4. EDELCAT 33 ELLIOT KEY

  5. Sailing and Snorkeling Key West Reef with Lungs of Tar Ep.3

  6. Sailing Florida Keys Backcountry Ocean Adventure- iboats.com

COMMENTS

  1. Catamaran Sailing Vacations in Florida

    Catamaran Sailing Vacations in Florida Keys: Upper and Lower Florida Keys - Dry Tortugas - Fort Lauderdale, Miami, Marathon and many different stops along the way! Charter a Catamaran with no crew and drive yourself or hire professional crew for your catamaran trip. The Florida Keys have become a popular destination for Americans looking for a ...

  2. Calypso Sailing

    Welcome to Calypso Sailing. Calypso Sailing was established in 1988 in the beautiful Florida Keys. With locations in both Key Largo and Key West we specialize in luxury sailing vacations on a range of Leopard Catamarans, both bareboat and Captained. Our monohull sailing charters can take groups of 6 to 38 on day, sunset and overnight trips ...

  3. Sailing Catamaran Sirius

    Marathon Florida Keys Fishing Experience . 10. Fishing Charters. from . $795.00. per group (up to 4) Guided Clear Kayak Eco-Tour of Sugarloaf Key (Near Key West) 188. Kayaking Tours. from . $75.00. per adult. ... The Sirius is a sailing catamaran that is very relaxing and really a great evening. You get to mingle with the other patrons while ...

  4. Explore & Sail The Florida Keys

    Sailing the Florida Keys is full of wonders if you take the time to explore. The Keys are a boating paradise with a subtropical climate and SE winds most of the year. There are wonderful fishing, snorkeling, and diving destinations all within a day's sail. The Dry Tortugas, a US National Park made mostly of open water and 6 small islands, is ...

  5. THE TOP 10 Key West Catamaran Cruises (UPDATED 2024)

    Key West Small-Group Sunset Sail with Wine. 981. Escape to the still waters off the coast of Key West on this small-group, sunset wine-tasting cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers.

  6. Private Catamaran Sailing Charters Key West Florida

    Private 4th of July Champagne Sunset and Fireworks Party Cruise - 2 Hours. Your PRIVATE celebration for up to 12 guests! (No Concierge bookings) BOOK NOW. Catamaran Echo - Wild Dolphins! Snorkel & Sailing Adventure. Our 1/2 Day Trip only 1/2 Full Maximum. (4-14 passengers)

  7. Key West Sailing Charters

    Experience the beauty and wonder of an unspoiled tropical paradise without ever leaving the Continental United States. Our Key West sailing charter destination is located minutes from all the downtown Key West attractions and Duval Street night life, yet a short sail away from pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas.

  8. Florida Keys Yacht Charters & Sailing Vacations

    The Florida Keys possess everything necessary to have a dream vacation. Please note: This base is seasonally closed September 7 - 21. This base is also closed July 4th, November 25th, and December 25th. You must be qualified to sail in this destination. Please submit a Captain's Resume and a First Mate Resume before booking this destination.

  9. Crewed Sailing Catamaran Charter

    Searching for a reputible crewed sailing catamaran charter for a vacation or event? The Space Between is a 5 star rated, beautiful Leopard 46 that boasts all the upgrades and ammenities you are seeking in a charter yacht. Day sails available in Ft. Lauderdale, multi day in S FL, Keys and Bahamas.

  10. Sailing Catamarans for Charter in Key West

    Sailing Catamarans Tamboo Bali 4.2 Sailing Catamaran Key West Base 4 Cabins / 4 Baths / 2 Showers 8 Max Passengers (Including Captain & Crew) Details Eeya Leopard 40 ... The Florida Keys. Miami, Bahamas & Florida West Coast. Learn to Sail; Yacht Management; Request Quote; Sailing Catamarans TODscott 2023-03-07T12:48:18-05:00. Sailing Catamarans.

  11. Florida Keys Bareboat & Crewed Yacht Charters

    From Indian Key, it's a further 20nm sailing distance to Key Largo. Apart from the shops, bars and restaurants, most of the attractions are aquatic-based as they are all along the Keys. A visit to the Florida Keys Wild Bird Rehabilitation Center can be rewarding, a reminder of the fragility of nature in this delicate place.

  12. Sailing Catamaran "Sirius"

    11th Street Ocean Marathon, FL. For information and reservations call today (305) 304-2982. Discover and enjoy the luxury of personalized attention as you and the entire family experience a safe and relaxing sail aboard the sailing catamaran "Sirius". Sign up early - limited seating!

  13. Catamaran Charter in Key West, FL

    Get the best sailing deals on top boat rentals and yacht charters in Florida! ... Come Sail the Florida Keys with Lagoon 42! Key West • Bareboat 42 feet • 8 guests • Lagoon • 42 • 2018 $8,414 (per week) Have fun in the sun on this Florida catamaran charter. Key West • Bareboat ...

  14. About Calypso Sailing in Key Largo, Florida

    About Calypso Sailing. Calypso sailing is owned and operated by Lance and Suzanne Holmquist. They offer a range of ways to charter beginning your journey in the amazing Florida Keys. CATAMARAN CHARTERS Catamaran sailing vacations aboard our 58 Leopard Lady Susan and our two Leopard 44 models Big Easy II and Second Star.

  15. Sailing Charters in Key Largo and Florida Keys

    The Bloody Pirate is a beautiful schooner sailing in the beautiful Florida Keys. She is named after the famous Code Rum cocktail drink. Enjoy an exciting Keys sailing adventure and watch us hoist her red sails on a true tall ship.. She can accommodate intimate private parties or large groups up to 38 people for day charters or 24 overnight.

  16. Florida Yacht Charters & Sailing Vacations

    Sailing conditions in Florida are excellent, particularly around the Florida Keys. The best time to set sail is between January-April where you'll experience wins of around 15-20 knots, ideal for sailing! Florida's hurricane season is between June-November so you may choose to wait until the Spring for your vacation.

  17. Sailing the Florida Keys: 2 week Florida Keys Sailing itinerary

    Florida Keys Sailing Guide: A 2 week itinerary. 1. Sailing from Dinner Key to Rodriguez Key. 49 Nautical Miles // 8 hours of sailing. If you decide to spend the first night of your journey at Dinner Key, the city has moorings available for $29.16 a night for vessels under 40 feet.

  18. Florida Bareboat & Captain Yacht Charters

    Come Sail the Florida Keys with us! READY. SET. SAIL THE FLORIDA KEYS At the end of a 110-mile-long chain of islands, stretched like a string of pearls across a Caribbean blue sea lies charmed Key West, it is here you will find Florida Yachts Charters. ... We will be happy to consult with you about our yacht management options in the Florida ...

  19. Top 7 Best Florida Keys Sailing Tips

    So, make sure you consider sailing during the off-peak season. The sunsets are one of the best I've ever seen. 2. Charter a Boat To Reach More Destinations. While sailing the Florida Keys, you may consider stopping along the way to stay at hotels. This is a valid choice, but it can really slow you down.

  20. Catamaran Sailing the Florida Keys

    We sail on a friend's lagoon 42 in the Florida keys.Charter with Brad,Https://www.restlessnative.comThis channel is funded by viewers like you. Please help ...

  21. Florida Keys Sailing Charters

    This greatly increased human settlement of the Keys. The railroad was destroyed by a hurricane in 1935, but in 1938 the longest over-water road in the world was built on the railroad's foundation. It includes 42 bridges--one that is seven miles long! This opened the Florida Keys up to a growing tourist trade. Book Now

  22. A Guide To Sailing In The Florida Keys

    A Guide to Sailing in the Florida Keys. There are over 880 reasons why the Florida Keys are the best yacht charter destination in America. This endless chain of coral islands wiggles from Miami to Key West in a sandy necklace licked by the sun. Only 30 of the islands are populated - mainly by lucky park rangers and oyster shack shuckers.

  23. Sailing adventure in the Florida keys

    Sailing The Space Between is a family run boat charter in Fort Lauderdale. Experienced and unique escapade on a Key West Catamaran trip. Dream vacation with catamaran rental in Florida.

  24. The top 3 adventures in The Florida Keys & Key West

    A 125-mile-long archipelago at the southernmost tip of the US, the Florida Keys are made up of around 1,700 laid-back islands. Stretching like a string of pearls across the teal waters of the Gulf ...