Key West Yacht Rentals - Private Charters & Cruises

Experience the yacht lifestyle on the Mia in beautiful Key West, FL.

key west yacht charters

Mia Yacht Key West

Key West Yacht rentals is more than a brokerage service. We are a wealth of local knowledge with superior service to ensure your Key West Yacht experience is one to remember. We love making new friends and creating awesome memories. The MIA is a well-appointed 90 ft Cortenzo yacht built in 2009 and completely refitted in 2020. It is berthed at beautiful Stock Island Marina village with all its great amenities. The MIA with its 4 staterooms beautiful salon and comfortable media center is cozy comfortable which lends itself to all that Key West and its beautiful water offer. We pride ourselves on building custom packages for all our guests. Our attention to detail is paramount in allowing you to sit back and relax and enjoy all that Key West and its surrounding unique lifestyle.

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The Mia Services

All cruises are BYOB for alcoholic beverages, food or snacks. A chef can be provided if desired to prepare your special meal, additional info and cost will be provided upon request. Full galley, grill, coolers, ice, bottled water, sodas, glasses and place settings, utensils, blender, and crew is provided. ​Sunset times vary throughout the year, for times available click please send a request for your desired dates.

All cruises and routes are subject to change due to docking, weather or current conditions, USCG restrictions or Captains' discretion.

key west yacht charters

Take A Video Tour

The Mia Yacht in Key West was a wonderful experience for our family, beautiful memories were made. Top notch service, would highly recommend to anyone. A trip out to Boca Grande Island is a must if you’re visiting...The atmosphere of Stock Island Marina was amazing, lots of amenities. Truly a wonderful place to gather on any occasion. We definitely will be returning.

Best Day Ever!! Owner Mike and Captain Ryan and crew are the pinnacle of service and professionalism. If you like 1st class service and beautiful accommodations, Mia is the boat for you.

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The Mia - Key West Yacht Rental & Charters

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After Hours Key West Logo

Welcome to the Best Private Yacht Charter in Key West

Boating is a way of life in southern Florida. When you’re visiting on vacation, you can elevate your experience by spending time on the water. At After Hours, we provide a selection of boat tours with private boat charters in Key West to give you the boating experience you need to enjoy true vacation bliss during your time in the Keys. Whether you’ve been searching for the best sunset cruise or want to take a day trip to enjoy fun in the sun with the opportunity to see dolphins and other marine life, we have the options you need for the ultimate experience.

Enjoy Our Specially Designed Boat Tours

Whether you’re interested in a sunset cruise to enjoy the tranquility of a beautiful sunset in the Keys or want to take a day trip that introduces you to local wildlife while you take in the sights from a unique perspective, our boat tours will give you the ultimate experience. Our experienced captains know the best places to take you to walk on pristine private beaches, swim in crystal clear waters, or even snorkel with sea turtles. We work hard to give you and your group the most amazing experience possible. We even include customized catering while you’re onboard with us.

Get a Private Boating Experience

When you book a private yacht charter with us, we will pamper you with the best experience you could dream of. We’ll help you leave the real world and the crowds behind, so you feel like you’re the only person on the planet. A private boat charter is ideal for heading out for some solitude or sharing an intimate experience with that special someone, your family, or a close group of friends. We customize each experience based on your preferences, so you’ll have the time of your life!

If you’re looking to make your Key West vacation extraordinary, we have the solution. After Hours is a private yacht charter that can take you and your guests to vacation bliss.

Why Choose After Hours?

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Key West Yacht Charter on After Hours

Yacht

Welcome aboard After Hours

You work hard. Your vacation days are precious. Why spend them in a crowd?

Your perfect day in paradise is custom-made to give you the pampering you need. This is your chance to break away from the masses and go beyond the ordinary.

On A Private Yacht

You left your hectic life behind to take a vacation. Why spend it in a crowd? Let us pamper you with a day, evening, or extended cruise in private luxury. Onboard After Hours, you’ll enjoy food and drink tailored to your tastes as you leave the real world (and its crowds) behind.

Drinks

With Your Special Guests

Imagine hosting your closest friends and family for an amazing outing that they’ll remember for years. Or show your important clients or colleagues how much they are valued with a one-of-a-kind experience. Or even pop the question in a way that almost guarantees a “YES!” with a romantic proposal trip. Life’s big moments deserve special treatment. 

Your Trip, Your Way

Sunset cruise.

SunSet

Key West sunsets are legendary. But, imagine a private sunset cruise during your visit to Key West. Sunsets are one of the most romantic experiences in Key West. Get away from the crowds and make it special on your own private charter.

Scuba

You’ll never forget your After Hours day trip in Key West, FL. Cruise to a secluded island with crystal clear waters. We can be your escape to adventures based on what you want. Walk on a secluded beach? We know the best ones. Snorkle with sea turtles? Let us introduce you.

Key West Events

After Hours Charter

There’s always a festival or holiday being celebrated in Key West. What better way to participate than aboard After Hours private yacht charter. Sunset cruises or day trips, you’ll never forget this private yacht charter in Key West.

Yachting in Key West, FL

Located at Florida's southern tip, Key West captivates with azure seas, vibrant coral reefs, and a relaxed vibe. Experience the island's allure and enjoy luxury yachting in Key West, FL. Perfect for leisurely cruises or thrilling adventures, Key West is ideal for sun-filled coastal experiences. Discover its beauty from the deck of your private yacht.

52 Viking Princess luxury charter yacht - Galleon Marina, 619 Front St, Key West, FL 33040, USA

52' Viking Princess

80 FF Pendleton luxury charter yacht - Key West, FL, USA

80' FF Pendleton

75 Multihull luxury charter yacht - Key West, FL, USA

75' Luxe Catamaran

Why charter a yacht in key west, fl, traverse hidden treasures with key west luxury yacht charters, boat rental in key west, .css-1uazooj{display:-webkit-box;display:-webkit-flex;display:-ms-flexbox;display:flex;-webkit-align-items:center;-webkit-box-align:center;-ms-flex-align:center;align-items:center;width:100%;outline:2px solid transparent;outline-offset:2px;transition-property:var(--chakra-transition-property-common);transition-duration:var(--chakra-transition-duration-normal);font-size:1rem;-webkit-padding-start:var(--chakra-space-4);padding-inline-start:var(--chakra-space-4);-webkit-padding-end:var(--chakra-space-4);padding-inline-end:var(--chakra-space-4);padding-top:var(--chakra-space-2);padding-bottom:var(--chakra-space-2);padding:10px 16px;}.css-1uazooj:focus-visible,.css-1uazooj[data-focus-visible]{box-shadow:var(--chakra-shadows-outline);}.css-1uazooj:hover,.css-1uazooj[data-hover]{background:var(--chakra-colors-blackalpha-50);}.css-1uazooj[disabled],.css-1uazooj[aria-disabled=true],.css-1uazooj[data-disabled]{opacity:0.4;cursor:not-allowed;} .css-1pkhz46{font-size:var(--chakra-fontsizes-sm);font-weight:600;-webkit-flex:1;-ms-flex:1;flex:1;text-align:left;} how do i book a yacht on yachtlife .css-g5ledl{width:1em;height:1em;display:inline-block;line-height:1em;-webkit-flex-shrink:0;-ms-flex-negative:0;flex-shrink:0;color:currentcolor;vertical-align:middle;font-size:8px;}, when is my payment collected is it refundable.

Once you confirm your reservation, your broker will process your payment.

  • If you are booking for a single day and your reservation is confirmed more than 7 days in advance, a deposit of either $1,000 USD or 50% of the total cost of the reservation (whichever is greater) is processed immediately in order to hold the yacht. Once your embarkation date is 7 days away, the remainder of the amount due is processed.
  • If you are booking for a single day and your reservation is made 7 days or less in advance, the total price of your reservation is processed immediately.
  • If you are booking for a multi-day charter and your reservation is confirmed more than 30 days in advance, a deposit of 50% of the cost of the yacht is processed immediately in order to hold the yacht. Once your embarkation date is 30 days away, the other 50% is collected for the price of the yacht, plus the APA, plus the taxes due.

Terms of refunds are dictated by the Charter Agreement. Generally, once a payment is collected, it is non-refundable. In certain circumstances, as dictated by the Charter Agreement, credits can be provided so you will be able to enjoy your yacht charter at a future date that is convenient for you.

Why is there a 3% credit card convenience charge?

Are my payment details saved on the app, what if your servers get hacked is my payment information really safe.

key west yacht charters

Private & Shared Sailing Charters

Sunset sail key west.

Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.

key west yacht charters

Get inspired with our most popular trips!

Private sunset sail.

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Chillout Lilypad Sail

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Key West Daysail

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Sunset Sail on When & If

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Privates Charters

Discover your perfect private charter.

Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.

key west yacht charters

Shared Trips

Come together on a shared charter.

Rise above the crush of the crowds and set sail on a unique shared sunset charter, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.

key west yacht charters

Three Classic Boats

View our fleet.

We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.

Real. Fun. Sailing.

key west yacht charters

When And If is back at beautiful Stock Island Marina!

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Check Out Our Ship's Store!

key west yacht charters

Wreckers' Race Season Is Back!

key west yacht charters

Hello, Sailor! Don’t miss out on the latest Sunset Sail news & offers.

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Friends of SSKW

Legal & safety.

Keys YachtCharter.com  Key  West  Luxury  Yacht  Charters

Key West      Lower Keys      Back Country     Sand Bars       Atlantic      Fishing      Sunsets

Schedule your next fishing trip with us... Mahi, Tuna, Wahoo...

Don't miss our sunsets! The Florida Keys are known for some of the BEST sunsets

The best place to spend your weekends with or without the Kids!!!

Need a Boat?

Contact us for  availability

© 2021 Owned and Operated by Key West Luxury Yacht Charters, LLC. DBA - Keysyachtcharter.com. All rights reserved

Charter.com

Want a Slide Boat?

Available for charter, 2020 - nauticstar 231 hybrid, length - 22' 9" / 6.93 m , beam - 102" / 2.59 m, maximum hp w/seastar steering -  250 hp / 186 kw, transom height - twins  - 25", approximate draft -  13" / 0.33 m, deadrise @ transom - 13° , deadrise @ entry - 35°   , approximate weight   - 2650 lb / 1202 kg, *fuel capacity   - 74 gal / 280 l , in-console livewell/baitwell  -  15 gal / 57 l, aft livewell (port side)  - 27 gal / 102 l , aft fish box   - 50 gal / 189 l   , persons/total weight   - 10/1350 lb / 612 kg, max weight capacity   - 1854 lb / 841 kg, for sale profitable opportunity  the exquisite 1991 46 pilothouse charter boat.

(305) 831-4125

Yacht 42 - 2.jpg

Welcome Aboard Motor Yacht 42!

Private luxury charters aboard a 60ft Angel Motor Yacht

The Ultimate Key West Experience

Yacht 42 provides the perfect entertaining space to celebrate special events such as birthdays, anniversaries, weddings, or just treat yourself to something special.

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A Unique Adventure

Escape the crowds, have your day tailored exactly as you like it, and make memories that will last a lifetime

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Charter Type Charter Type Deep Sea Fishing Charter Flats Fishing Charter Private Custom Charter Sailing Charter Large Group Charter Overnight Charter Sunset Charter Boat Rental Dry Tortugas Charter Luxury Yacht Charter Cuba Charter Jet Ski Rental Spearfishing Charter Snorkeling Scuba Diving Glass Bottom Boat Dolphin Watching Corporate Boat Party Lobstering Charter Wedding Charter Film Production Charter Other

Duration Duration Half Day (4hrs) 3/4 Day (6hrs) Full Day (8hrs) Multiple Day

Number Of Participants Number Of Participants 1 2 3 4 5 6 More Than 6

Location Location Key West (Lower Keys) Islamorada / Marathon (Middle Keys) Key Largo (Upper Keys) Dry Tortugas Cuba Other...

Date(s) Of Charter

Girl on beach snorkels during a Stay on a boat in Key West trip.

Best Key West Boat Charters

#1 in key west boat charters.

   Hello and welcome to the best boat charter site in beautiful Key West Florida. With over 100 years of charter experience in the Key West waters, our crews provide that local touch you just can’t find anywhere else. I guess you could say Key West boat charters are just in our blood!

   Private charters, sunset sails, Dry Tortugas, boat rentals, fishing and more, no matter what boat excursion you’re seeking we’ve got you covered. Catering to our guest’s every need is just a part of what makes our Key West boat charters the best in the business.

   So make yourself at home and feel free to browse our site with confidence, knowing you’ve made the right choice.  We make it our personal mission to provide our guests with a charter experience of a lifetime. Thanks for choosing Key West Charter Boat and welcome to the Florida Keys.

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(305) 783-2430

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Marlin jumps during a Key West boat charters offshore Fishing trip

Custom Fishing

Custom Fishing Trips…

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Luxury Yachts

The Best Or Nothing…

Man spearfishing for Mahi Mahi with Key West Boat Party

Key West Charter Boat,

3200 Harriet Ave,

Key West, FL 33040

United States Of America

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Phone: (305) 587-3499 Email: [email protected]

Fun In The Sun Key West, FL.

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Key West Yacht Rental

43′ Luxury Charter Boat

Please call to confirm captain availability before booking online., try something a little different. a luxury charter aboard our 43′ charter boat the lisa lynn..

Sunset Cruises | Day Trips | Multi-Day Charters

The Lisa Lynn is a beautiful 43′ Luxury Charter Boat with 4 staterooms and 2 baths. Lisa Lynn can comfortably host up to 12, and sleep up to 6 passengers. This is the perfect boat to take on a private luxury snorkeling trip to one of our amazing reefs, or a sunset cruise to entertain friends and family. The yacht is available for custom charters, including a variety of Sunset & Day Cruises and Multi-day Trips to the islands. The Lisa Lynn is also available as a stay-aboard vacation rental boat if you’re looking for a new adventure. We can have the boat stocked with preferred food and drinks by one of our local caterers or you can bring your own provisions. We provide cooler and fridge space, and bottled waters. Paddleboards, inflatable dock, snorkel gear, and sno cone machine provided on all day trips (not on sunset cruises).

Lisa Lynn boat and crew pricing-

6 passengers or less:, (fuel, tax, and crew is included, 3% fee on credit cards), overnighter 26hrs-$3750, multi-day: call for pricing, stay at the dock as a hotel: $300 a night for up to 2 people, $50 per person extra per night after 2 people, plus tax. 6 people max. $175 cleaning fee. , 7-12 passengers:, (bareboat rental with crew contact list ), *boat fee includes fuel and tax, we collect boat fee, 3% fee on credit cards, *crew fee is total for captain and mate, you pay them directly, 2hrs- $950 (boat fee $650, crew $300), 3hrs- $1195 (boat fee $795, crew $400), 4hrs- $1595 (boat fee $1095, crew $500), 6hrs- $2095 (boat fee $1395, crew $700), 8hrs- $2445 (boat fee $1595, crew $850).

(All drivers of the vessel must hold a captain’s license, have logged local experience, and have been trained by our staff on the operation of the vessel. All drivers on our approved list have met these requirements. We will provide a crew list and crew availability after reserving the vessel. For more details on the structure of our bareboat rentals please navigate to our 7-12 passenger charter page. Renter must sign a bareboat charter agreement and be 25yrs or older.)

Please call or send us a message to confirm availability before booking your charter aboard our Luxury Key West Charter Boat.

Blue Ocean Yacht Charters

Bareboat Charter Key West

by "Charter Booker" | Dec 19, 2017 | Yacht Charter

Bareboat Charter Key West

1. Determine when you want to go on a Key West Bareboat Charter

Knowing when you plan to travel helps determine the cruising grounds you should be considering. Prices, availability and particularly weather, can all vary depending on the time of year and can play an important part in choosing a Key West Yacht Bareboat Charter destination.

2. Determine what type of Bareboat Charter in Key West

Is this a family holiday, quiet romantic getaway, a couple’s or singles trip, etc.? This will determine what type of boat and crew would be suitable, and what islands to visit or activities to plan for on a Key West yacht Bareboat Charter

3. Determine where you want to go on your Bareboat Charter Key West

Yacht charters are available around the globe with The Caribbean and Key West being the most popular. After hurricane, Irma and Maria’s devastation in the Caribbean more potential bareboat yacht charter customers are looking to Key West.  The Dry Tortugas and Fort Jefferson remains the most popular destination from Key West for a Bareboat Charter.  https://www.nps.gov/drto/index.htm

4. Determine your Key West Bareboat Charter budget.

Price plays a part in most people’s yacht charter. Our staff will help you maximize your budget and may in fact help you get more yacht than you thought possible for a Key West Yacht Bareboat Charter.

5. Determine what style of charter fits your Bareboat Charter Key West.

There are 3 types of a boat charter in key west:, – a crewed yacht charter:.

Your yacht comes with a permanent captain and cook. Price includes all meals and often house wines and open bar. Meals are prepared to your taste (to a very high standard) from individual preferences given to the cook before the charter. You choose the day’s activities and the itinerary, on a day to day basis. Yachts tend to be more luxurious and have more ‘toys’ (kayaks, waterskis, A/C, entertainment centers, etc) than a bareboat charter. The cost per person can be close to or less than the cost on a crowded cruise ship. Matching your party to a suitable crew is an important part of our service. Blue Ocean Yacht Charters currently does not offer Crewed Yacht Charters.

– Bareboat Yacht Charter Key West:

Sail the boat yourself. The principal charterer needs to have skippering experience on a yacht close to the size you are chartering. Equipment standards and reliability can vary considerably, even within a company. It is a mistake to choose a boat purely by price and the cheapest boat is not always the best value.

You can also charter through a bareboat company and add a captain (and cook). This is the ideal way to bareboat charter in Key West. Let us help you find a captain that is familiar with the boat and sit back and relax. Most captains will allow experienced sailors to operate the yacht on their own under the supervision of the captain. Typically boat owners will allow a lower deposit if a bareboat charter customer hires a captain that is familiar with the boat.

Now that you’ve decided the boat charter Key West, the fun really begins. There are so many yachts for you to choose from. Which one is right for you? Our staff knows each and every one of them, and once we know your desires for a dream yacht charter, Blue Ocean Yacht Charters will handle Step 6 for you.

6. Research & narrow your Boat Charter Key West choices.

Our staff will make suggestions and help you narrow down your private boat charter choices. We will do this based on your requirements and our personal knowledge of each boat and cruising ground.

7. Interview the prospective crews and recent charterers.

For a crewed charter, we feel the selection of the crew is actually more important than the boat. A good crew can make up for a mediocre boat but the opposite is not true. We maintain relationships with all yachts and closely monitor feedback from our recent charterers, so we are in an excellent position to find the perfect match for you and your guests.

For bareboat charters, the condition of the boat and the back up services provided by the company are very important as well.

8. Once you’ve decided, inspect the current condition of the yacht.

Any boat and /or crew can look good in a brochure or website. Some are immaculate and some are maintenance nightmares. 3 years of bareboat chartering can cause the same wear as 10-15 years of private use, but with a crewed yacht, maintenance is more important than age. We have inspected every boat you are chartering and can describe its current condition in Key West for a bareboat charter.

9. Arrange the other details.

You’ll need hotel reservations, provisioning options, customs and passport requirements, itineraries, airline tickets, etc… We can recommend and/or handle all of this for you and because of our volume discounts, can probably save you money by bundling your airfare with your Key West yacht charter.

10. And finally…step on board.

Put on your sunglasses, take off your sandals, relax, unwind and enjoy on a private boat charter in Key West.  You’ll be remembering this vacation for a lifetime. For real peace of mind, let us do it for you.  https://blueoceanyachtcharters.com/our-yachts/

Have a fun bareboat charter and be safe.

“Charter Booker!”

(Charter Booker, manages Blue Ocean Yacht Charters in Key West and writes many of the company’s blogs.  Having experience both on the water and off the water helping customers experience the best possible yacht charter for many years.  Charter Booker carries American Sailing Association certifications and has extensive knowledge of boat safety and regulations.  Call 305-923-4152 and ask for “Charter Booker” when booking your next yacht charter with Blue Ocean Yacht Charters in Key West, Florida.)

  • Private Yacht Charters

Call for more info 305-890-6485 Get started with our online form

April 22, 2015 by [email protected]

Key West Private Yacht Charter & Boat Charters

Our boat is a unique event space in Key West for a private boat charter. This certainly is the perfect way to dazzle your clients, employees, friends or family. Charter our yacht and cruise (or sail) through Key West with us.  Sail alongside the Dolphins or catch a glimpse of the famous Key West “Green Flash” at sunset. Not only is this a unique event space but is the best way to host a party. 

For your Key West private yacht charter we have the beautiful 105 foot Schooner  America 2.0.  The Schooner America 2.0 was built for performance. For this very reason you will experience the exhilarating feeling of sailing aboard this stunning 105 foot sailboat. 

We are located in the historic Old Town Key West.  Our cruises will depart from the Key West Bight which is directly behind the Schooner Wharf Bar. We will take you out into the emerald green waters of Key West for an event you are sure to never forget.  

To sum it up, our yacht is perfect for a variety of ideas and will fit your every need.  It is is perfect for just you and your loved one to celebrate your milestone anniversary, for celebrating a beautiful marriage or even a family reunion.  Let our professional crew treat you like royalty and cater to your every need. So step aboard and join us for a Key West Sail!  

Key West Mimosa Sail

Private Morning Sail on Schooner America 2.0

Step aboard the stunning America 2.0 for a Key West Morning Charter. This 1.5 hour sail is available to book privately with your close friends and family. Start your day off right and take the helm and experience the power of this sailing machine or sit back and relax as you sail smoothly through the crystal clear waters of Key West. Either way and above all, it doesn’t get much better for a morning sail in Key West.  Options to extend your trip are available. Charter includes soda, juice, and water. Bar and food packages are available upon request. (Call us directly to save 6% online processing fee)

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Schooner America 2.0

The Schooner America 2.0 »

New york, ny and key west, fl.

Offering our most premium sailing experience, Schooner America 2.0 is the newest, largest, most elegant vessel designed for Classic Harbor Line. Added to the Classic Harbor Line fleet in 2011, America 2.0 offers the most exceptional day sailing one can find. She is the fastest, most refined, and the most comfortable schooner of the fleet.

Read More about the Schooner America 2.0 Oct-May in Key West, FL » Read More about the Schooner America 2.0 June-Sep in New York, NY  

Learn More About Private Charter Rates »

Why host a Private Charter?

key west yacht charters

Nautical Weddings »

Classic Harbor Line: Known as the boutique of Key West yachts, boasts the elegant and legendary Schooner America 2.0 . This yacht is known for its quality craftsmanship, and its intimate, elegant and comfortable environment. From the Schooners’ beautiful sails and construction, to the experience of sailing through the emerald green waters of Key West this is a yacht for taste and style.

Read More about Nautical Key West Weddings »

key west yacht charters

Corporate Events »

Classic Harbor Line has constructed and hosted a variety of Corporate and Small office functions for the entertainment and excitement for you and all your colleagues. These yachts are a unique way to host your Key West corporate yacht charter! Your employees, clients and friends will never forget the experience.

Read More about Corporate Events »

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Corporate Teambuilding »

Perfect for any corporate team-building event, the Schooner America 2.0 has a fun, competitive, and educational team-building program. With hands-on activities, teams will not only have a great time but will also collectively learn about the basics of sailing and line-handling.

Read More about Teambuilding »

key west yacht charters

Birthdays »

Made another trip around the sun? Then it is time to celebrate under the sun aboard on of our classic sailboat, America 2.0 . Grab your friends and family to celebrate the big 3-O, 4-O, 5-O, or even the 1 double-O! All ages are welcome aboard for a celebration to last the ages.

key west yacht charters

Holiday Parties »

‘Tis the Season for Holiday Parties! Join us on the Luxury Schooner America 2.0 for your office holiday party, family gathering, or night out with friends; our classic yacht is sure to dazzle even your pickiest of guests. The Schooner America 2.0 is best during the Holiday Season to accommodate 20 – 76 guests. So throw a classic Key West Holiday boat party for your favorite people.

key west yacht charters

Meetings and Conferences »

Think outside of the box for your next meeting or conference. This unique meeting space with the famous Key West Sunset as your backdrop will be sure to impress. The dazzling Schooner America 2.0 can facilitate meetings, seminars, sales conferences, networking events and client meetings for 20-76.

key west yacht charters

Whether you are interested in wine and cheese or making the perfect cocktail you will be sure to love these fun events aboard our classic yacht. Jump into the wonderful world of wine aboard the Schooner America 2.0 and enjoy a Key West Sunset while educating yourself in a fun manner!

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See our calendar of events, private yacht charters.

Private Yacht Charters

Sail out into the emerald green waters of Key West and impress your guests. Step aboard the legendary Schooner America 2.0 for a private charter. This yacht is perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

PUBLIC EVENTS

Public events

Sail out into NY Harbor and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

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Captain Charter

Sit back and relax on your own private yacht while a professional takes the helm to show you the best of the Florida Keys. We offer multi-night yacht charter vacations. All of our Captain Charters have a minimum of 5 days/4nights which is the ideal amount of time to experience one of our Florida Keys sailing itineraries . Learn more about what to expect aboard a Captain Charter with Florida Yachts Charters.

Captain Selection

Captains, cooks & mates, life aboard, family friendly & kids aboard.

We are required under USCG regulations that define bareboat charter to allow you to choose your own captain. We will not assign one for you. We can provide more information of those captains who are familiar with our operations, the waters of the Florida Keys and our vessels. Should you already have a captain we require they complete our captain’s application for approval.

Captains, Cooks & Mates, Oh My!

Unless you are on a sailing course, when you interview potential captains to hire for your charter, they will ask you about prior boating experience and your ability in assisting with things like, picking up moorings balls, anchoring, dock lines and ability to manage the vessel in an emergency situation . If no one aboard would qualify to fulfill the role of 1st mate they will require you also hire a mate. Some mates can act as cook for an additional rate while others are only able to act as a mate. Adding a cook means they take care of all the meal planning, provisioning, cooking and clean up, a splendid addition to your experience. If you are unfamiliar with provisioning and cooking aboard a vessel this is a highly recommended choice.

Captains generally charge $450-500 a day, first mates $250 & Cooks $275.00, plus their food & beverages. For Cooks, they charge a full day for planning & provisioning time before your charter start. A 15 – 20% gratuity is industry standard for services well rendered.

Life Aboard a Captain Charter in the Florida Keys

Life aboard a yacht in the Florida Keys can take you to some beautiful anchorages, snorkel sights and secluded beaches. Your yacht will have all the comforts of a boutique hotel. The galley has just about everything your kitchen at home has so cooking aboard will be seamless. Refrigeration aboard vessels is much smaller than at home, and monohulls have very tiny freezer space. While all our vessels are equipped with Generators and ACs for comfort at anchor, while underway you will not be able to run the Generator, therefore you will not have AC until you reach a mooring ball or anchorage for the night. Most guests open the hatches while underway for a nice tropical breeze. As a result of Covid, we have taken the decision to not supply masks & snorkels for safety reasons over sanitation. We do sell good qualify snorkel/masks set and rent fins. We have local companies that can rent paddleboards & kayaks.

Families & Kids Aboard your Captain Charter

Key West & the Florida Keys is a great family friendly boating destination. The captains in this area know all the best places for spotting dolphins, snorkeling and a relaxing night at anchor. For safety reasons there are few things to note about having kids aboard when considering a captain charter with children:

  • Bring along or plan to buy children’s life jackets. They are weight specific up to a certain age and we don’t offer them. Children are required to wear a life vest at all times while on deck, if your children have never worn a life jacket we recommend purchasing ahead of time and practice wearing, otherwise they will be stuck below deck with an adult.
  • Our captains are professional and great with kids but it is important that a parent, guardian or designated adult keep an eye on them at all times. Your captain and mate will be very busy attending to navigation, sailing, and everyone’s overall safety and should not be relied upon to be watching children should you be absent. There are many things for kids to bump their heads on, interesting buttons to push and lines to grab. An interesting tip we recently read to ensure authority has been passed from one parent/guardian to the next is to use the phrase “Your Jane and John” and make sure the other adult responds “My Jane and John;” inserting your kids names into this phrase of course. This way you know that they know you are no longer watching the kids. If you are a pilot you may be familiar with this tip, as it was modified by parents who were former pilots for around the water safety at home.
  • It may also be a good idea to talk with your kids (depending on the age) about power, water and toilet management. You will potentially be away from the dock for several days at a time. All our vessels are equipped with Generators and AC’s but these items are additional amenities and should there be a mechanical failure you may not have access to additional power and AC until it can be repaired. Depending on your itinerary you may also be without WiFi or cell phone access from time to time.

6651 Maloney Ave, Unit 1 Key West, FL 33040

[email protected] 800-650-6940

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ALWAYS ON THE SHORE

7 Best Key West Private Boat Charters In 2024!

by waynekask | Dec 21, 2023 | Blog , Key West | 0 comments

The best Key West private boat charters in 2023

Last Updated on December 21, 2023

Always On The Shore contains affiliate links and is a member of the Amazon Services LLC Associates Program.  If you make a purchase, we make a small commission at no cost to you. For more information, please read the disclaimer page . 

Are you looking for the top Key West private boat charters? If so, you’ve come to the right place!

Whether you’re looking for a half-day or full-day charter, boat trips to a private island, or a crew offering the most perfect hospitality, this list has something for you.

As an expert on Florida travel and a Sunshine State fanatic, I’ve carefully curated this list of Key West private boat charters to include only the best of the best.

Let’s dive in!

Don’t Have Time To Read The Full Article? Book The Private Half-Day Key West Boat Trip   with a 5 ⭐️ rating

Our Top 3 Picks: Key West Private Boat Tours!

a woman sitting on a paddle board in the turquoise waters of Key West during a Half Day boat trip

Private Half Day Key West Boat Trip

a woman in her swimsuit posing in the sand bar beach with a tiki bar boat cruise at the background

Private Sand Bar Cruise On A Tiki Bar Boat

private charter boat sailing during a beautiful sunset in Key West

Private Wind & Wine Sunset Sail In Key West

Best Key West Private Boat Charters!

1. snorkel, sandbar & dolphin excursion in a glass-bottom boat.

a man standing above a private boat charter on the crystal blue waters of Key West in Florida

Photo Credit- Floridays

Tour Rating: 5 Stars ⭐️⭐️⭐️⭐️⭐️     Length: 3.5 Hours      Check Rates Here

Make your Key West vacation extra special with one of the most distinctive charter boats available: a glass-bottom boat .

There is no better way to see Florida’s coral barrier reef and fabulously diverse sea life than through the glass on this private charter with your own captain.

Enjoy a day trip into the Florida Keys National Marine Sanctuary to snorkel.

All the while, your crew will share their wealth of local knowledge about the ocean.

Next, you’ll head to a remote island where you can explore, paddleboard, snorkel, or float in the crystal blue waters.

If you’re lucky, you may even get in some dolphin watching!

This unique experience gives you the opportunity to enjoy aspects of the natural environment many tourists never see.

Here’s what a past guest said about this tour:

“This was the single best charter boat experience we’ve ever had. Ashley, the captain, was stellar… Ashley is a great captain and she’s fun intelligent and interesting, but she also knows her craft… Of all the things we did in Key West, this was absolutely the highlight of the trip and worth every penny… Such a fantastic experience.”

Melody_K ⭐ ⭐ ⭐ ⭐ ⭐

✅ What’s included in this tour: 

Bottled water

Use of Snorkeling equipment

Cooler with Ice

Book this Snorkel, Sandbar & Dolphin Excursion In A Glass-Bottom Boat

2. Private Wind And Wine Sunset Sail In Key West

a private boat charter in Key West along the beautiful sunset background

Photo Credit- Danger Charters

Tour Rating: 5 Stars ⭐ ⭐ ⭐ ⭐ ⭐     Length: 2 Hours      Check Rates Here

Turn your trip into a special occasion with a private sunset cruise in Key West .

Spend two hours relaxing on a 65-foot schooner near Opal Key Resort with great music and even greater views. 

Soak in the views while you sip on international wines, beers, and non-alcoholic beverages (full bar style).

Snack on delicious hors d’oeuvres, take pictures and chat with the crew.

Watch a spectacular sunset over the waters of Key West to finish off a perfect day.

Sophistication and beauty define this private sailing charter. You’re sure to have an amazing time.

Note: The departure time is just before sunset.

“This is the second time I went on the Wind and Wine Sail… it’s top-notch customer service and not too crowded. The wine and snacks are great and the crew is so personable. Definitely recommend this trip!!”

Tripadvisor Reviewer ⭐ ⭐ ⭐ ⭐ ⭐

✅ What’s included in this tour:

Alcoholic Beverages

Hors d’oeuvres

Book this Private Wind And Wine Sunset Sail In Key West

3. Private Dry Tortugas Luxury Charter In Key West/ Lower Keys

man reading a book in a private luxury charter boat in Key West

Photo Credit- SeaEO – Nautical Ventures

Tour Rating: 5 Stars ⭐ ⭐ ⭐ ⭐ ⭐     Length: 8 Hours      Check Rates Here

Ready for an unforgettable experience? If so, step aboard this Luxury Charter full-day tour to ensure you have enough time to do everything you want.

The captain and crew will tailor the boat ride and itinerary to your preferences.

Whether you’re looking for an intimate experience involving sunsets, want to spearfish your own lunch, snorkel above a coral reef, or visit your own private sandbar, the decision is up to you!

One option is to head to the remote and beautiful Dry Tortugas–a group of islands featuring an exceptional natural habitat.

Here you’ll find glorious white sand, beautiful waters, and historic Fort Jefferson.

It’s the perfect destination for an all-day adventure and is on many people’s bucket list.

When it comes to full-day charters in the lower Florida Keys, this is definitely one of the best.

“We had the most incredible afternoon with SeaEO and Carlos. He took us to a sandbar where we drank champagne in the ocean and watched the sun go down. Truly an unforgettable experience. Carlos tailored every moment of the experience to our wishes. We will call him every time we are in Key West from now on.”

Mary_C ⭐ ⭐ ⭐ ⭐ ⭐

Air-conditioned vehicle

Restroom on board

WiFi on board

Private transportation

Use of Snorkel equipment

Use of spear gun

  √ Book this   Private Dry Tortugas Luxury Charter In Key West/ Lower Keys

4. Private Luxury Sailing Catamaran Charter

a woman in yellow beach dress wearing a beach hat on board a luxury private charter boat

Photo Credit- Bimini Charters

Tour Rating: 5 Stars ⭐ ⭐ ⭐ ⭐ ⭐     Length: 3 Hours      Check Rates Here

Wind, sea, and sails await on the private luxury catamaran tour .

Choose the best time for you, or opt for a dreamy afternoon sail over the crystal clear waters surrounding Key West.

Keep an eye out for sea turtles and dolphins, relax on the trampolines, or sip on cocktails while the breeze blows softly past.

You can also don snorkel gear and explore the underwater world.

This catamaran charter is a perfect way to enjoy a special day with your partner, celebrate family get-togethers, or simply celebrate life.

Rest secure in the extensive experience of your captain. This day will be worry-free and fabulous.

Snorkel, sail, and delight in the views on one of the most popular sailing charters available.

“Sitting in the netting of the catamaran and watching the water go by the snorkeling was awesome. We went out to the reefs. He was able to post up while we snorkeled.”

Jonathan_D ⭐ ⭐ ⭐ ⭐ ⭐

3-Hour Boat Tour

Book this Private Luxury Sailing Catamaran Charter

5. Private Half-Day Key West Boat Trip

Photo Credit- Native Sun Private Charters

Tour Rating: 5 Stars ⭐ ⭐ ⭐ ⭐ ⭐     Length: 4 Hours      Check Rates Here

Have a blast on the gorgeous Key West waters on this private half-day boating experience .

This boat is a one-stop shop for pure  fun . You can snorkel among tropical fish, paddle board, make sandbar trips, or even enjoy a little fishing.

Whether you’re looking for a relaxing tour of Key West or jam-packed hours of activity, this tour could make for the best day of your life.

Charter lengths can vary from 2 to 8-hour day trips, but at 4 hours, this tour could be a perfect option.

It lets you enjoy the sunshine and sea but still have half a day for other activities or pure relaxation.

“You can’t go wrong with this excursion! Captain Tim was an excellent captain and guide!! His boat and the service he provided were top-notch. All of the equipment was in great condition, and he was very knowledgeable about the best places to go for the water activities we wanted to partake in. We would love to do this again the next time we’re in Key West!”

Sarah_S ⭐ ⭐ ⭐ ⭐ ⭐

Soft drink/Pop

Use of snorkel gear

Fishing gear

Paddleboard

Book this Private Half-Day Key West Boat Trip

6. Private Sand Bar Cruise On A Tiki Bar Boat

Photo Credit- Tiki Boat Adventures

Skip the chaos of larger group sailing tours and enjoy a great day on a private Tiki boat .

A tiki boat is the perfect vessel for bachelorette parties, groups of friends, and anyone who enjoys exploring.

Join one of these Tiki sandbar tours and sip or snack on whatever food or beverages you bring along.

Keep an eye out for dolphins, turtles, and other marine life as you cruise.

This tour passes by the US Navy facilities and cool landmarks, visits Jewfish Basin (an amazing area for wildlife), and cruises into the backcountry of the Florida Keys.

“What a great time! Plenty of shade aboard which was great. The captain was a stitch! Took us through just beautiful little islands where we swam and explored a bit. Perfect half-day trip!”

Kyle_H ⭐ ⭐ ⭐ ⭐ ⭐

Ice, Cups, water

Book this Private Sand Bar Cruise On A Tiki Bar Boat

7. Private Key West Sunset Cruise

2 guests sitting on a chair i front of a private cruise or boat while watching the beautiful sunset in Key West FL

One of the best experiences you can have in Key West is watching the sunset from the quiet waters of the Gulf.

Sail through a working harbor, explore mangroves, and even try your hand at fishing.

Next, your captain will take you to one of the best spots to see the sunset.

Gorgeous views and tasty snacks and sips make this sunset charter a fabulous choice.

If you’re ready, book your charter today and enjoy an unparalleled trip through North America’s natural treasures.

When it comes to multi-activity charters, the customer service and reviews set this private charter apart.

“Great night! Loved our experience. The boat moved slowly, we saw parts of Key West we hadn’t seen and learned a few things, too. The only negative was the boat is a bit older but it got the job done for a beautiful night watching a Key West sunset! Thank you!”

Suzanne_H ⭐ ⭐ ⭐ ⭐ ⭐

Book this Private Key West Sunset Cruise

aerial view of a luxury private boat cruise

Key West Private Boat Charters – Frequently Asked Questions

How much is a private charter in key west.

Private charters in Key West range from approximately $725 dollars per group of up to six people to $4,000 or more for a group of up to 15 people.

Private charters are a great way to experience the natural beauty of Key West.

How Much Does It Cost To Charter A Boat In Key West?

The cost of chartering a boat in Key West ranges from approximately $725 dollars per group of up to six people to $4,000 or more for a group of up to 15 people.

Can You Take A Private Boat To Dry Tortugas?

Yes! You can take a private boat to Dry Tortugas.

Simply check out  #3 on this list  and book your private adventure to the beautiful remote islands of Dry Tortuga National Park. It’ll be the adventure of a lifetime.

What Does A Private Charter Boat Mean?

A private boat charter is similar to boat rentals, but you won’t have to drive the boat yourself. 

Instead, you’ll have a captain (and sometimes additional crew) to man the boat.

You can enjoy a delightful day on the water without worrying about logistics or the technicalities of boating (and no massive size groups detracting from the experience).

You also get to decide where you want to go and what activities you’d like to do during the day.

How Much Does It Cost To Take A Boat To Dry Tortugas?

It costs about $200 per person to get to Dry Tortugas on the public ferry from Key West.

However, you can also get there via a private sailing catamaran. One  private charter option costs $1,899.00 per group of 12 people.

How Do I Get To Dry Tortugas Private Charter?

You can get to Dry Tortugas via a private charter by booking this  Private Dry Tortugas Luxury Charter in Key West/Lower Keys .

the best private boat charters in Key West

Final Thoughts: Key West Private Boat Charters

Have a great time away from home on these amazing Key West Private boat charters.

They are perfect for corporate events, family outings, and romantic getaways.

From yachts and catamarans to floating tiki bars and glass-bottom boats, this list has something for everyone.

Enjoy a day sailing through the Keys with the company of your choice.

Still Haven’t Decided? I Recommend Private Key West Half-Day Boat Trip  with a 5 ⭐️ rating

Booking a last-minute trip to Key West Florida?  

If so, we have you covered.  

Top Tours in Key West  – Viator

Top Rated Hotels & Accommodations –  Booking.com

Looking To Get Around In Key West Florida?  

Check out rental car rates here! 🚗

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The Best Shark Tour In Key West For 2024!

Key West Kayaking Tours: 5 Highest-Rated In 2024!

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FORT JEFFERSON & DRY TORTUGAS

key west yacht charters

HAVANA FLEET

Express day trips & multi-day charters.

key west yacht charters

CHARTER YOUR DREAM BOAT AND EXPERIENCE THE ADVENTURE OF A LIFETIME

Live in the sunshine, swim in the sea, drink the wild air. Fort Jefferson & The Dry Tortugas are located 70 miles west of Key West and are only accessible by boat or seaplane. Our Ft. Jefferson Day trip offers travelers the chance to visit this remote national park in one day. Travel in comfort aboard our ultra-fast center console charter boat Havana Sky. We can accommodate up to 6 guests on the charter, with multiple options for activities once at the destination. This charter allows guests the chance to take the journey of a lifetime in a single afternoon. Or charter a multi-day trip aboard the Havana Moon for up to 12 guests, and experience this natural wonder from your very own private yacht.

Fort Jefferson & Dry Tortugas Private Charter

Fort Jefferson is a must-see for anyone visiting Key West. This massive brick fortress is one of the most important historical landmarks in the United States. Its original purpose was to protect this strategic sea location along the world’s busiest shipping routes as the United States expanded into the Caribbean. It also provided ships a place to resupply, repair, or seek refuge from tropical storms as they patrolled the Gulf of Mexico or the Straits of Florida.

As you stroll along the white sandy beaches of Fort Jefferson, Key West, take in the calming island breeze. This Great American landmark is located on Garden Key in the Dry Tortugas and boasts some of the most beautiful beaches in the world.

A private charter to the Dry Tortugas grants guests a chance to view this historical landmark with minimum encroachment by large tour groups. Once the day-trip boats go home, you will have the opportunity of touring the fort without the crowds. According to the National Parks Service, the Dry Tortugas National Park is also one of the few naturally dark areas in the country, offering some of the best star gazing in the USA.

Explore the largest island in the Dry Tortugas, Loggerhead Key. Named for its abundance of loggerhead sea turtles, Loggerhead Key has long been a haven for wildlife. The site of shipwrecks, a significant lighthouse installation, and where the historic Carnegie Laboratory for Marine Ecology once stood. Guests can snorkel the surrounding waters, which offer some of the most pristine reefs in the world.

START THE JOURNEY

Let's plan a custom Key West Charter together. Use the contact form below to tell us a little more about your trip.

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COMMENTS

  1. Blue Ocean Yacht Charters

    Rent a private luxury yacht or sailing boat for a day or a multi-day charter in Key West and the Florida Keys. Enjoy the natural beauty, coral reefs, and sunsets of the Dry Tortugas and the Florida Keys with Blue Ocean Yacht Charters.

  2. Key West Yacht Rentals

    Enjoy a sunset cruise or a week-long voyage through the islands with Key West Yacht Rentals. Choose from our fleet of beautiful private yachts for your customized event or dream vacation.

  3. Florida Keys Yacht Charters & Sailing Vacations

    Sail the southernmost point of the continental USA with The Moorings and explore its coral reefs, beaches, and history. Choose from different yachts and itineraries and enjoy the tropical vibes of Key West and Dry Tortugas National Park.

  4. Private Yacht Charter Key West

    Enjoy a private boat charter in Key West with After Hours Yacht Charters. Customize your trip with sunset cruises, day trips, or private tours to see dolphins, sea turtles, and more. Relax on a private yacht with customized catering and catering.

  5. Luxury & Private Yacht Charter Key West, FL

    Beyond the scenic beauty, a yacht charter in Key West opens the door to a realm of water adventures. Dive into activities such as snorkeling, fishing, and more, immersing yourself in the vibrant marine ecosystem. Enjoy the privacy and comfort aboard your yacht, whether it's a romantic escape, a family retreat, or a celebration with friends.

  6. Yacht Charter Key West

    Blue Ocean Yacht Charters offers a variety of yachts for charter in Key West, Florida, with quality performance, accommodations, and customer service. Whether you want to sail, motor, or enjoy the sun, you can choose from a fleet of boats that suit your needs and budget.

  7. Sunset Sail Key West

    Welcome to Sunset Sail Key West, Key West's most versatile custom charter experience. With three beautiful vintage boats, great local captains and crew, and the pristine waters of the Florida Keys at our disposal, we're confident that we'll have everything you need to make your dream sail come true.

  8. Key West Yacht Rentals

    Enjoy the luxury and convenience of a Key West yacht charter, with options for family vacations, corporate events, or sportfishing. Choose from a variety of sizes and designs, from 38-foot catamarans to 200-foot motor yachts, and explore the Florida Keys' natural beauty and wildlife.

  9. Havana Fleet Luxury Charters Key West

    Enjoy a once-in-a-lifetime experience onboard one of our luxury charter boats, custom-tailored to your needs and specifications. Choose from three different vessels, each with its own features and activities, and explore the stunning destinations of the Dry Tortugas and Loggerhead Key.

  10. Key West Luxury Yacht Charters LLC

    Length - 22' 9" / 6.93 M Beam - 102" / 2.59 M Maximum HP w/SeaStar Steering - 250 HP / 186 kW Transom Height - Twins - 25" Approximate Draft - 13" / 0.33 M Deadrise @ Transom - 13° Deadrise @ Entry - 35° Approximate Weight - 2650 lb / 1202 KG *Fuel Capacity - 74 Gal / 280 L In-Console Livewell/Baitwell - 15 Gal / 57 L Aft Livewell (port side) - 27 Gal / 102 L

  11. Florida Bareboat & Captain Yacht Charters

    Florida Yachts Charters offers a variety of yacht charter options in the Florida Keys, from bareboat and captained charter to sailing instruction and yacht management. Whether you want to explore the Florida Keys on your own, with a crew, or learn to sail, you can find your perfect yacht and experience the charm of Key West.

  12. Key West Sailing Itinerary

    This structure stands 109 feet tall above the waterline and is a marvel to view. Make time for a stop at another beautiful coral reef for snorkeling on your way back towards Key West. Please make sure to notify the base of you imminent arrival to the fuel dock. Make sure to arrive before 5:30 pm for fueling and pump out.

  13. Key West Yacht Charter

    Escape the Key West crowds, have your charter on our yacht tailored exactly as you like it, and make memories that will last a lifetime! ... Custom Yacht Charters. Email: [email protected] Tel: (305) 831-4125. Our Location. Perry Marina. 7001 Shrimp Rd. Key West, FL 33040. Ask the Crew. First Name. Last Name. Email.

  14. Key West Charter Boat

    With over 100 years of charter experience in the Key West waters, our crews provide that local touch you just can't find anywhere else. I guess you could say Key West boat charters are just in our blood! Private charters, sunset sails, Dry Tortugas, boat rentals, fishing and more, no matter what boat excursion you're seeking we've got you ...

  15. Yacht Charters

    Our luxury yacht charters are unmatched. Reward yourself and your loved ones with an unforgettable experience aboard our yacht. Havana Fleet will set you on a luxurious personalized charter out of beautiful and sunny Key West, Florida. Our private luxury charter is meticulously curated, so each experience leaves our valued guests satisfied.

  16. Key West Yacht Charters

    A luxury charter aboard our 43′ Charter Boat The Lisa Lynn. The Lisa Lynn is a beautiful 43′ Luxury Charter Boat with 4 staterooms and 2 baths. Lisa Lynn can comfortably host up to 12, and sleep up to 6 passengers. This is the perfect boat to take on a private luxury snorkeling trip to one of our amazing reefs, or a sunset cruise to ...

  17. Bareboat Charter Key West

    Charter Booker carries American Sailing Association certifications and has extensive knowledge of boat safety and regulations. Call 305-923-4152 and ask for "Charter Booker" when booking your next yacht charter with Blue Ocean Yacht Charters in Key West, Florida.)

  18. Key West Boat Charters

    Key West Boat Charters is more than a brokerage service. We are a wealth of local knowledge with superior service to ensure your Key West experience is one to remember. We pride ourselves on building custom packages for all of our guests. Our attention to detail is paramount in allowing you to sit back and relax and enjoy all that Key West and ...

  19. Key West Private Yacht Charter & Boat Charters. The perfect Sunset Sail!

    Charter our yacht and cruise (or sail) through Key West with us. Sail alongside the Dolphins or catch a glimpse of the famous Key West "Green Flash" at sunset. Not only is this a unique event space but is the best way to host a party. For your Key West private yacht charter we have the beautiful 105 foot Schooner America 2.0.

  20. 6 Best Yacht Charters In Key West, Florida

    View properties in Key West. 3. Happy's Houseboat (from USD 550) Show all photos. This private yacht charter in Key West is perfect for a couple seeking a unique getaway on the water. Anchored in an enclosed bay, this houseboat has a spacious main suite and a well-equipped kitchen.

  21. Key West Captained & Crewed Charters

    Captained and crewed yacht charter vacation in the Florida Keys and Key West. Step aboard, sit back and relax on your private charter. ... 6651 Maloney Ave, Unit 1 Key West, FL 33040 [email protected] 800-650-6940.

  22. 7 Best Key West Private Boat Charters In 2024!

    5. Private Half-Day Key West Boat Trip. Photo Credit- Native Sun Private Charters. Tour Rating: 5 Stars ⭐⭐⭐⭐⭐ Length: 4 Hours Check Rates Here. Have a blast on the gorgeous Key West waters on this private half-day boating experience. This boat is a one-stop shop for pure fun.

  23. Fort Jefferson & Dry Tortugas

    Fort Jefferson & The Dry Tortugas are located 70 miles west of Key West and are only accessible by boat or seaplane. Our Ft. Jefferson Day trip offers travelers the chance to visit this remote national park in one day. Travel in comfort aboard our ultra-fast center console charter boat Havana Sky. We can accommodate up to 6 guests on the ...