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Key West Sailboat Charter Aboard the Tamboo

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Our Fleet: the Tamboo

Bareboat or captained charter ~ asa sailing courses*, ocean's edge marina key west, florida 2023 bali 4.2 sailing catamaran 4 cabins - 4 toilets w/sinks - 2 showers 8 passengers max. or 6 passengers maximum if charterer selects and pays for a captain., *charterer selects and pays for an asa qualified captain for asa training..

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Specifications

Cabins/berths Toilet w/sink Shower stalls

Beam Draft Water Capacity Fuel Capacity Engine

4 - (8 occupants max.)

23'6"

5' 227 US Gal 169 US Gal

2 x 45HP Yanmar

Interior Features

Air Conditioning

Interior Fans

Generator power

Solar power

Fridge/Freezer

Freshwater Filter

3 burner cooktop

Freshwater electric toilets

Exterior Features

Cockpit Cushions

Bimini Over Helm

Dinghy on Boat Lift

Forward Lounge

Swim ladder

Helm Lounge

Built in BBQ Grill

Fully Equipped Galley

Dishware, Silverware, Cutlery, Cooking Utensils

Serving bowls, platters, pitcher, cookware

Cutting Boards (*please provide your own cutting board, filet knife & cooler for fish*)

Small Appliances such as Coffee Maker,

Blender, Toaster, Microwave

Starter supply of paper towels, dish soap, fresh sponge

Linens & Things ​

Bed Sheets & Blankets (beds will be fully dressed upon arrival)

2 Bath, Wash & Hand Towels per guest

Starter supply of marine grade toilet paper

Navigation Equipment

Apparent wind indicator

Depth sounder

RAYMARINE AXIOM+ GPS/chart plotter

Hand Bearing Compass

Parallel rulers

Stereo/cockpit speakers

VHF mic at helm

Local charts

Cruising Guide to Florida Keys

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Blue Ocean Yacht Charters

 Key West & Marathon, Florida

We specialize in private luxury yacht & sailing charters at affordable prices. we offer day charters as well as multi-day charters., why blue ocean yacht charters.

Blue Ocean Yacht Charters, located in Key West, Florida, makes yacht rentals affordable and life-changing.  We offer private multi-day bareboat charters to amazing destinations like The Dry Tortugas and the Florida Keys.  Just looking for a day charter?  Look no further.  We offer four hour, eight hour, and 24 hour charters as well multi-day charters.

All our yachts come fully equipped to make your private boat charter experience what you’re looking for. We offer motor and sailing yachts that provide the best boat rental experience.  

Bareboat Charters

Key west bareboat charters - perfect for 6-12 guests.

Are you looking for a charter in Key West for more than 6 Passengers?  Look no further!   Casual Monday Charters is now offering Bareboat Charters for up to 12 guests.

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What is a Bareboat Charter?

A Bareboat Charter is a type of arrangement in the boating industry where an individual or group rents a boat without Captain, crew or provisions included. Essentially, the charterer becomes the responsible party and is responsible for operating the vessel, planning the itinerary, and ensuring the safety of all onboard. This type of charter is ideal for those seeking a more independent and customizable boating experience. 

Bareboat Charters offer the freedom to explore various destinations at your own pace and create a unique adventure on the water.

For most bareboat charters in the Florida Keys we recommend hiring a qualified captain to pilot the vessel, most owners that we work with will require this.  We are happy to provide a list of all pre-qualified captains on every vessel listed.

It is important to remember when hiring a bareboat charter that you as the Charterer are responsible for hiring the captain, provisioning the boat.  Ice, Water, Snacks, Fuel and Captain are not included.

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Cobia 296 Center Console

This well equipped 2017 Cobia 296 Center Console is available now for the 2024 charter season.

Up To 10 Passengers

Twin Yamaha 300’s  Onboard Head (bathroom) Comfortable Seating Dual Simrad chartplotters

No Pets No Smoking This vessel requires a qualified Captain to operate.   See our list of captains here.

Bareboat Charter Pricing

This 2017 Cobia 296 is available for half day (4 hour) or Full Day (8 hour) Charters.

Half Day pricing – $850 + Captain Full Day $1250 + Captain

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What To Bring On A Key West Bareboat Charter

Here’s a list of a few items you’ll want to make sure you grab before setting off on your  Key West Bareboat charter . • Hats • Beach towels • Sunscreen (please no spray on) • Sunglasses • Cameras (make sure they’re waterproof or safely in a secure case!) • Alcoholic Beverages (BYOB) • Food or snacks you might want for your trip – All Documents provided by the Charter Broker – Contact info for your Captain and Crew

What Not to Bring • More than 11 friends (12 passengers maximum) • Glass bottles • Red Wine

To book this vessel reach out to Captain Zak via Email, Text, or Phone and he can set you up for the perfect day on the water.

A Note From Captain Zak

I’m just a guy with a boat. I love Key West and having a good time on the water—  whether sandbar hopping, diving, fishing, or just enjoying one of those famous Key West  sunset cruises. So let me know what you’d like to do during your stay here, and we’ll put  together a sandbar cruise in Key West that you and your crew will never forget. So come  on down and let me show you my backyard playground — the Fabulous Florida Keys. Captain Zak From somewhere warm —and yet really cool— aboard the Casual Monday

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Come Enjoy our smooth riding ocean going 25 ft Hydrasports center console upgraded with twin 200 EFI engines. Whether you’re looking to jump in the water at the sandbar and turn up the JL Audio system while you enjoy a cold one or make a quick and comfortable ride out to the reef our boat is just right for the occasion.

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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. 

bareboat sailboat charter key west

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. 

Browse our yachts for charter in Florida Keys

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

The Essential Guide to Sailing Holiday Charters

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

Enquire about a charter...

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.

bareboat sailboat charter key west

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Private Liveaboard Classes

Florida keys sailing, come sail with us.

bareboat sailboat charter key west

Proud Member of the ASA

At Florida Keys Sailing our specialty is: Private Live Aboard Sailing Classes and Sailing Vacations with just you and your spouse or friends. “Learn to Sail” or take an Advanced Class to develop your skills. Qualified sailors can Charter our boats. A Captain will happily take you and your family on a Day Sailing Trip if you need one. Many sailing classes offered elsewhere crowd you on a boat with a group of total strangers.

At Florida Keys Sailing ALL of our Sailing Classes, Day Sailing Trips, and Private Charters are exactly that…PRIVATE.

No one else except YOUR Party is ever on-board. This means you will learn more by having more time DOING, not WATCHING someone else sail. Dollar for dollar you will find more VALUE in taking your Sailing Courses at Florida Keys Sailing.

Fun on the Waves

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Our Classes

To learn more about the liveaboard classes we offer, visit our classes page

2 DAY BASIC FUNDAMENTALS OF SAILING

Designed for beginners who want the best introduction to the exciting sport of sailing. Students will receive a good understanding of all the “Basic Fundamentals of Sailing”. They will leave as very competent Crew Members.

3 DAY BASIC KEELBOAT “LEARN TO SAIL CLASS”

Beginner students will learn to responsibly be the Skipper of a Day Sailing Keelboat in familiar waters in moderate wind and sea conditions. Classes available are year round on demand based on your travel plans.

5 DAY BASIC COASTAL CRUISING OR 101 & 103

Students will learn to responsibly skipper and crew an auxiliary powered cruising sailboat during daylight hours within sight of land in moderate wind conditions. This Private Live Aboard Class is taught aboard our Catalina 30' or Irwin 34 Offered all year on demand based on your travel plans.

5 DAY BAREBOAT CRUISING OR 103 & 104

Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34. Offered all year on demand based on your travel plans. 5 Days and 4 Nights…Privately Living aboard at our Dock

3/1 DAY ADVANCED COASTAL CRUISING OR 106

Cruise a sailboat during nighttime hours in most wind and sea conditions. A Private Live Aboard Class is held aboard our Catalina 30 or Irwin 34. Offered all year on demand based on your travel plans. 3 Days and 3 Nights…Privately Living Aboard

7 DAY BAREBOAT CRUISING OR 101, 103 &104

Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34 This is the Class the Bareboat Charter Companies want you to have. Offered all year long on demand based on your travel plans. 7 Days and 6 Nights…Privately Living Aboard at our Dock

3 DAY FAST TACK TO CRUISING ASA 101 & 103

It’s the fastest and least expensive way to get the first 2 – ASA Certifications. Both combined into a 3 Day / 2 Night Live aboard Class. Prior sailing experience before enrolling is advised.

5 - DAY FAST TACK TO BAREBOAT CRUISING ASA 101, 103 & 104

It’s the fastest and least expensive way to get these 3 - ASA Certifications. All 3 are combined into a 5 Day / 4 Night – Live aboard Class. Prior sailing experience before enrolling is advised. A second student enrolls for FREE!

Testimonials

Daysailing & charters, we offer both daysailing and charters, click below to learn more.

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  • SAILING LOCATION: Keys Fisheries & Marina 35th St Gulfside, MM 49 Marathon, FL 33050
  • By Mail: Florida Keys Sailing 5171 Overseas Hwy #504407 Marathon, FL 33050
  • By E-Mail: [email protected]
  • By Telephone: 305-619-0140
  • Marathon Chamber of Commerce
  • Get Knotted - Animated Knots
  • Sombrero Lighthouse Data and Marine Forecast

Copyright© 2020 Florida Keys Sailing™, LLC

bareboat sailboat charter key west

Florida Keys Best Yacht Sales and Charters

Charter a  catamaran plan your own private key west sailing adventure, day charters, 4-8 hours ​, multi-day charters, bare boat charters, crew available ​.

Buy or Sell A Catamaran

Brand New Build

Power or Sail

Vessels in any category

Sailing School

Take a learning vacation! 

We offer 101, 103, 104, 114, 106

bareboat sailboat charter key west

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.

bareboat sailboat charter key west

Get inspired with our most popular trips!

Private sunset sail.

bareboat sailboat charter key west

Chillout Lilypad Sail

bareboat sailboat charter key west

Key West Daysail

bareboat sailboat charter key west

Sunset Sail on When & If

bareboat sailboat charter key west

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.

bareboat sailboat charter key west

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.

bareboat sailboat charter key west

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.

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When And If is back at beautiful Stock Island Marina!

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Check Out Our Ship's Store!

bareboat sailboat charter key west

Wreckers' Race Season Is Back!

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

bareboat sailboat charter key west

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Sail Away Catamarans

Half Day Bareboat Charter

This charter lasts 4 hours from the time you cast off your lines from the dock until you return and may include fueling time. A suggested activity for this charter is to sail or motor to the coral reefs nearby (45-60 mins. one way), grab a mooring ball, and snorkel. Another activity would be to learn how to sail or drive the yacht. Dolphin encounters are common in Key West as well as sea turtle sightings. To wrap up the day, many customers take in a sunset sail or motor cruise. With so many things to see and do, charter customers find it nearly impossible to do everything in a half day yacht charter.

key-west-Full-Day-Bareboat

Full Day Bareboat Charter

Everything that you can do in a half day with double the time! Popular activities on an eight hour bareboat charter may include: snorkeling, sunset sail, dolphin encounters, touring Key West, ocean side. If you are not one for getting wet in the ocean, touring Key West Oceanside is amazing. To end your day, close out with a sunset sail!

The Dry Tortugas National Park and Ft Jefferson Destinations

(special restrictions may apply)

Taking a bareboat charter for a round trip from Key West to the Dry Tortugas National Park and Ft. Jefferson is a once in a lifetime experience.  We will connect you with a catamaran that exceeds all your expectations.

The Dry Tortugas and Ft. Jefferson are located 70 miles west of Key West. There are no stores or places to provision on your way therefore it is recommended to provision prior to leaving the docks. Your first night can be spent familiarizing yourself with the yacht and unpacking as well as taking in a drink at the tiki bars featured at The Perry Hotel and Marina. Plan on leaving the docks first thing in the morning.

Marquesas Keys

Sail 30 miles west of Key west and spend your second night at the Marquesas Keys. Here you will find a beautiful uninhabited island chain located halfway between Key West and the Dry Tortugas. At the Marquesas Keys, you will enjoy white sandy beaches to walk, explore, and swim. Dolphins have been seen enjoying this anchorage as well as you and your boat. From your yacht you can take the dinghy to and around the island. The Marquesas Keys are an amazing stop for some peace and serenity where you rarely will see another boat.

The Dry Tortugas and Fort Jefferson

On day three enjoy a sail through the clear blue water of the Gulf of Mexico. Once you arrive at Garden Key in The Dry Tortugas National Park, drop your anchor, and dinghy into the beach to check in with a park ranger. Make sure to get the latest updates and weather reports. Enjoy a vacation away from technology distractions as there are no cell towers at the Dry Tortugas. Take time to learn the park rules and regulations, then stop in and see the museum and gift store. End the day at the top of the wall that surrounds Ft. Jefferson taking in a beautiful sunset over Loggerhead Key.

Fort Jefferson

As you awake on day four take time and enjoy the wildlife around you. Beautiful clear water will give you visibility of tropical fish swimming around you in Garden Key. Enjoy learning about the historic landmark of Fort Jefferson and the millions of bricks needed to build this military base. Hear the story of the famous doctor that was imprisoned here for plotting President Lincoln’s assassination and then later discovered a cure for malaria. You will gain so much knowledge on a tour of Fort Jefferson. It is highly recommended!

Loggerhead Key and The Windjammer Wreck

If your schedule allows, set sail for Loggerhead Key. This is where you can see the only lighthouse in the Dry Tortugas National Park. Loggerhead Key is a beautiful island that you can swim from the beach and snorkel the famous Windjammer Wreck. This wreck is over 150 years old and is the only wreck that protrudes out of the water. Its an amazing snorkel to see beautiful corals and tropical fish. In the evening, enjoy the Fort, walk to the moat or relax on the yacht with unbelievable views. Make sure to enjoy all the stars at night as they are magical and unlike anything you have ever seen.

Embark back to the Marquesas Keys

If you have time, enjoy the other amazing keys and islands in the Dry Tortugas. When ready, head back to Key West stopping once again at the Marquesas Keys. Enjoy a relaxing sail along the way. Remember to arrive early enough at Key West before the fuel dock closes.

Head back to Key West

After a good night's rest, enjoy some additional time at the beautiful Marquesas Keys or pull anchor and head back to Key West. Remember to arrive early enough before the fuel dock closes.

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Florida Keys Yacht Charter

Embark on a unique yacht charter adventure in Key West and the Dry Tortugas. Discover history, pristine natural beauty, and thrilling offshore passages.

Discover the Florida Keys

Florida Keys & Key West: A charterers' delight with vibrant city life, the remote Dry Tortugas National Park, and underwater treasures waiting to be explored.

Key West offers more than just a lively city - it's a gateway to secluded Dry Tortugas, rich marine sanctuaries, and unforgettable offshore adventures.

Pirate's lair anchorage in the Exuma Bahamas

Chart your course with confidence

Explore our handcrafted Florida Keys sailing itinerary.

Sail from bustling Key West to serene Dry Tortugas. Dive into history at Fort Jefferson, snorkel at Windjammer Wreck, and savor the majestic sunsets over Marquesas Keys

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Florida Keys: explore what awaits you

Uncover the cruising conditions you can expect out there on the water and the various sailing seasons for this stunning destination.

Unlock in-depth Florida Keys yacht charter insights

Explore our latest Florida Keys blog posts to get a deeper understanding of its hidden gems.

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Summer reads: nautical adventures & high-seas thrills

To help build your summer reading list for those relaxing moments on the beach, I’d like to share some books I highly recommend that I’ve read in the past.

bareboat sailboat charter key west

What is the Distance from Key West to the Dry Tortugas?

Discover the distance from Key West to the Dry Tortugas in our guide including essential sailing insights for a successful yacht charter.

bareboat sailboat charter key west

Key West Bareboat Charter | Sailing Adventure to the Dry Tortgas

Our 2021 Key West bareboat charter and sailing adventure to the Dry Tortugas. Great fishing, long passages, and plenty of history.

Florida Keys frequently asked questions

Have more questions? Visit our comprehensive FAQ page for detailed answers to common Florida Keys charter questions.

Key West offers a variety of provisioning options, from supermarkets to specialty stores. Visitors should plan to stock up on necessities since there are no provisioning options in the Dry Tortugas.

Sailors can enjoy steady trade winds and warm, comfortable temperatures year-round in Key West, with the best sailing conditions from December to May, avoiding the peak of hurricane season from June to November.

During the hurricane season, it's crucial to monitor weather forecasts closely and have flexible plans, as tropical systems can develop rapidly, potentially affecting sailing itineraries.

Fishing in the Dry Tortugas National Park is regulated, with certain areas designated as no-take zones. Anglers must familiarize themselves with and adhere to these regulations to ensure sustainable fishing practices.

Anchoring is restricted to protect the coral reefs and marine habitats. Visitors must use designated mooring buoys in specific areas within the Dry Tortugas National Park to minimize environmental impact.

Explore pristine shores and hidden gems

Unveil the best of Florida Keys, from secluded beaches to enchanting islands and serene anchorages.

Explore pre-Civil War Fort Jefferson and pristine beaches in the remote Dry Tortugas National Park.

Dry Tortugas National Park

Explore pre-Civil War Fort Jefferson and pristine beaches in the remote Dry Tortugas National Park.

Discover the best marinas, provisioning options, nightlife, and anchorage spots in Key West for yacht charter crews, the gateway to the Dry Tortugas.

Discover the best marinas, provisioning options, nightlife, and anchorage spots in Key West for yacht charter crews, the gateway to the Dry Tortugas.

Explore the Bird Key Wreck in Dry Tortugas National Park. Discover the Brick Wreck's history, marine life, and snorkeling opportunities.

Bird Key Wreck

Explore the Bird Key Wreck in Dry Tortugas National Park. Discover the Brick Wreck's history, marine life, and snorkeling opportunities.

Florida Keys charter planning?

Consider booking with the Yacht Warriors.

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Book Key West Sailing Charters

Call Key West Charter Boat, fill out a quote form or book a public sail online.  Whichever you choose we’ll find the perfect vessel for you.

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A day sail through the harbor with Key West Sailing

More Sailing Info...

Island sailing destinations.

Lets Circumnavigate Sunset Key, the island of the rich and famous. Who knows who you could spot sunbathing on their private beach? For a sailing adventure, you’ll long remember, cruise past Chica Boca Key, home to Naval Air Station Key West. With any luck, a squadron of navy fighter jets will take off right in front of you, heading to their carrier in the Atlantic.

You always have the option of cruising around and dropping anchor whenever the mood suits. Sailing the Florida keys is a family-friendly activity with opportunities to kayak snorkel and explore just about anywhere. Dolphin watching is always a crowd-pleaser. Same for snorkeling North America’s only living coral reef. Designated a national marine sanctuary, the reef is teeming with colorful tropical fish, sea turtles, starfish, conch and hundreds of other aquatic creatures.

For a more adventurous experience, dive one of the many shipwrecks that dot the coastline around Key West. Several wrecks are in shallow enough water to explore with just snorkeling gear. While those lying in greater depths will require scuba diving experience. Whatever you do while Key West sailing, we recommend ending the day at Mallory Square in downtown Key West for a cold drink and excellent dining.

Dry Tortugas Sailing Charters

For some excellent mid-distance Key West sailing, head 70 miles west of key west (112 km west of key west) and you’ll reach a remarkable group of islands called the Dry Tortugas. Remote and isolated, the islands are almost entirely undeveloped by man and a haven for wildlife.

Rising out of deep waters in the Gulf of Mexico, the Dry Tortugas are a migration waypoint and breeding ground for hundreds of thousands of birds. Birding enthusiasts will definitely want to bring binoculars for spotting sooty terns, masked booby, and the magnificent frigate bird, to name a few. And anglers will want to bring their rods and reels. The fish population here is also impressive, with over a dozen species to catch, including blackfin tuna, grouper, wahoo, mahi-mahi, and sailfish.

Key West Sailing Charter Variety

Group charters are a great way to experience Key West sailing. Boat tours cater nearly any occasion, including wedding parties, holiday outings, corporate excursions, even themed events. Privately chartering a sailboat is easy.

Just tell Key West Charter Boat the size of your party, amenities you’re looking for, the desired length of cruise and any special requests you may have. We’ll put you on the perfect boat for a family reunion sunset cruise or a seagoing party for 50.

For a swashbuckling sailing adventure, commandeer your own pirate ship. Private charter the 1939 wooden schooner  When and If.   The boat belonged to World War II general George S. Patton, so it’s no surprise she’s fast and powerful. Guests are encouraged to join the crew in hoisting sails and trimming them up. You can even take the helm if you like, feeling the same exhilaration as Patton did over 80 years ago.

The Safest Sailing In Key West

As with anything on the water, safety comes first. Your sailing experience will determine what type and size boat you’re qualified to charter. Big catamarans and mono-hulls require extensive experience in similar type boats. With Key West Sailing there is no shortage in boat variety.

When you arrive, expect to spend part of the first day going over the entire boat with a certified captain. All operating systems will be reviewed, including lines, setting and retrieving sails, winch and helm operation, navigation and communication equipment, and all safety procedures.

Bareboat Charters & Multiday Trips

When Key West Sailing you will be asked to demonstrate your docking skills as well as any other handling maneuvers your charter company may require. Trips of a certain duration or distance will require you to file a sail plan and to notify your charter company with any changes to that plan while underway.

Please allow time at the end of your charter for a complete walk around with captain or charter company member. In order to ensure a great Key West sailing experience, we only book with charter outfits that maintain their boats in constant shipshape condition.

As Remote As You Like

   Sailing the Keys is as close to nature as you can get, with the wind as your power source and aqua green water as far as the eye can see. Perhaps Ponce de Leon was right after all, only instead of a fountain, there was the sea and waves and beaches as white as the wings of a gull.

Aboard a sailing vessel of any type or size, you feel young and adventurous, as if time is standing still, or maybe even going backwards. Is that really possible? If there’s any place on earth where it could be, it’s Key West.

Key West Sailing sailboat makes way

Public trips

Boat anchor

Key West Sailing – Family Trip

Friendly pirate charters cruise with Key West Sailing

Key West Sailing – Friendly Pirates

Clipper Ships cuts through the water with Key West Sailing

Key West Sailing – Clipper Ships

Relaxing in sailboat catamarans trampoline with Key West Sailing

Key West Sailing – Relaxing

Luxury Yacht Charters with Key West Sailing

Key West Sailing – Luxury Yacht Charters

People relax during a sunset sail with Key West Sailing

Key West Sailing – Sunset Sail Charters

Clipper Ships lounge during sunset with Key West Sailing

Key West Sailing – Sunset Boats

Best Charters Best Prices

A Marlin jumps during Key West Sailing

Yacht Sun Odyssey 440 for hire in Key West

  • Sun Odyssey 440 [Yacht Price incl. Taxes]
  • Cockpit cushion
  • Outboard engine for dinghy
  • Yacht Insurance
  • Barbeque Grill (gas)
  • Final cleaning
  • VAT or sales tax

Yacht Sun Odyssey 409 for rent in Key West

Yacht Sun Odyssey 409 for rent in Key West

  • Sun Odyssey 409 [Yacht Price incl. Taxes]

Yacht Sun Odyssey 449 for rent in Key West

Yacht Sun Odyssey 449 for rent in Key West

  • Sun Odyssey 449 [Yacht Price incl. Taxes]
  • Barbeque Grill
  • Internet connection

Sailboat Sun Odyssey 389 for hire in Key West

Sailboat Sun Odyssey 389 for hire in Key West

  • Sun Odyssey 389 [Yacht Price incl. Taxes]

Charter a sailingboat in Key West, Florida

Beautiful, sunny Key West in Florida , off the southern tip of the eastern United States is a perfect place for any type of vacation, but the absolute perfect place from which to take a sailing holiday. Charter a sailboat from Key West through Yachtico.com today by booking online to be on your way and see for yourself how amazing sailing in Key West really is.

Though Yachtico is still expanding the options available in Key West, there are several beautiful sailboats still ready to be chartered. The most commonly distributed sailboat for charter is a sloop, which is a mono-hull boat with a single mast and two sails. The boats available from Key West all feature the ability for at least four people to sleep, meaning you can have a lovely holiday with a few close friends, or set sail by yourself for some moments of peace and solitude.

Book online through Yachtico.com today to charter the right sailboat for your needs today. And have a fantastic time sailing the beautiful Caribbean Sea !

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Sailing Monohulls

Sun Odyssey 440 Exterior Lounge

Jeanneau Sun Odyssey 440 Sailing Monohull Key West Base 3 Cabins / 2 Bath 6 Max Passengers (Including Captain & Crew)

[email protected] 305-934-5295

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bareboat sailboat charter key west

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bareboat sailboat charter key west

is all superbly equipped and maintained for your comfort and safety. On these boats you will find extra amenities uncommon on other charter boats, such as air conditioning, generator, GPS, electric windlass, electric halyard winch, autopilot, CD players and more. Please keep in mind that skipper, hostess/cook, provisions and leisure equipment remain options to make your yachting vacation complete. For more information check out Please note that Tropical Yachts has a (Click for more info.) Please choose from our great selection, shown below in order of yacht size.

KEY WEST MONOHULL RENTALS

Key west catamaran rentals.

that will best suit your needs and budget. We have many Fully Crewed All Inclusive options available!

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SUGGESTED FLORIDA SAILING ITINERARIES

Lazy Days Vacation Rentals and Boat Charters

Lazy Days Vacation Rentals and Boat Rentals

Key west, florida, create memorable vacations with our rentals.

Come join us for a memorable Key West Vacation staying on our 60 ft Sailing Schooner Serenity or stay in our Dockside Cottage enjoying your day with a Kayak or SUP paddle in the Harbour. Rent the slide boat for a sandbar trip or book a private charter.

✓ Effortless booking, unforgettable stays

✓ Land or Sea

✓ Saves money and time

bareboat sailboat charter key west

Contact us today to book a stay, boat rental or a private charter.

(954)647-0343

nicholas@ keywestbareboatrentals.com

Book a overnight stay on a 60 ft schooner and experience what life is like living on a sailboat. Serenity also available for Sunset sails , Reef Trips, and Day Sails.

Pricing: Overnight Stays / Pricing: Charters

High Season: 450.00 per night / Sunset Sail: $ 600.00

Low Season: $350.00 per night / Reef Trip: $1,200.00 with lunch and a sunset sail.

Dockside Cottage

Book a overnight stay in a nautical cottage on the water.

High Season: 450.00 per night

Low Season: $350.00 per night

bareboat sailboat charter key west

Book an overnight stay on a 46 ft Hunter Sailboat and experience what life is like living on a sailboat. Huntress also available for Sunset sails, Reef Trips, Day Sails and available for Bareboat Charters.

Pricing: Overnight Stays / Bareboat Charters / Captained Charters:

High Season: 450.00 per night / High Season: $5000.00 for 7 nights / Sunset Sail: $600.00

Low Season: $350.00 per night / Low Season: $3500.00 for 7 nights / Reef Trip: $1,200.00

bareboat sailboat charter key west

Aqua Fresh / Barbasol

Rent one or both of our 14 ft Sunfish Sailboats for a fun day of sailing.

Pricing: 150.00 per stay

bareboat sailboat charter key west

T/T Lazy Days

Rent a 1978 Classic Boston Whaler equipped with a newer 4 stroke Yamaha Outboard to explore the harbor or use it to snorkel, spearfish and lobstering at the point of safe harbor which has excellent spots and corral heads to lobster and spearfish.

Pricing: 300.00 per stay / 150.00 per day. No stay required..

All pricing is subject to Florida 7.5% Sales Tax and subject to change.

bareboat sailboat charter key west

Rent our 30 ft Double Deck Slide Boat to explore the harbor and watch the Sunset, or use it to snorkel, spearfish and lobstering at the point of safe harbor which has excellent spots and corral heads to lobster and spearfish. Local Sandbar 20-minute boat ride. Moderate boating experience required. Includes Ice chest and a large floating mat.

Pricing: 350.00 for 4 hrs with no captain

600.00 for 4 hrs with a captain

100.00 for 2- Stand up Paddle Boards

All pricing is subject to Florida 7.5% Sales Tax and subject to change. Fuel charged at cost.

Slide In Dockside

Rent our 30 ft Double Deck Slide Boat at the dock. Boat does not leave the dock. Comes with 4- Standup Paddle Boards, 4- Kayaks, 2- 14 ft Sunfish Sailboat, Large Floating mat, large cooler, Bluetooth Speaker. Boat is dock where there is great swimming in crystal clear water, perfect spot to watch the sunset, easy boarding of the water toys. Great place to grill out and chill. Access to Marina facility’s, bath house.

Pricing: 250.00 Per Day

How do I book a rental?

Just contact our team, tell us about your rental preferences and we’ll quickly build a plan that fits your needs.

Can I change my reservation dates?

Yes, with 45 days advanced-notice you can change your reservation dates up-to two times without an additional fee.

What is your cancellation policy?

Reservations cancelled within 45 days are subject to full payment for one night’s stay. We do our best to work with you!

How does billing work?

We require a 50% down-payment at the time of booking and the remaining 50% is due 24 hours before your stay.

How do I manage my rental booking?

You can contact anytime to make any changes. We typically respond within the hour.

It’s simple! Browse our selection of properties and select the one you’re interested in. Then contact us.

bareboat sailboat charter key west

Need help choosing a rental?

Our travel experts are here to help! Contact us for personalized rental recommendations and advice.

bareboat sailboat charter key west

Relax and let us handle the details for your next vacation rental.

✓ Effortlessly reserve your dream rental with our easy booking process.

✓ Experience flawless events and memorable gatherings during your travels.

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Our charter advisors are here to assist you.

An expert will find you the best offers

Sailboat rental in Key West, United States

Rent a boat in Key West to expore the island. You can also rent a catmaran in Key West if you prefer.

Our other types of boats

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Find the best prices for boat rentals & yacht charters with or without a captain.

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Boat listings are checked regularly to guarantee the highest standards possible

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COMMENTS

  1. Key West Bareboat Charters

    Bareboat Charter. A bareboat charter means the charterer, as Captain, is solely responsible for the safe operation of the vessel, including all aspects of navigation, anchoring, docking, and controlling the vessel under sail or power. Key West is considered an advanced sailing destination and for the safety of other passengers and the vessel ...

  2. Key West Bareboat Charter

    Book your next Key West bareboat charter adventure at sea with Key West Cat Sail. Enjoy Dry Tortugas National Park, Looe Key Coral Reef, and other local destinations from the comfort of our 2023 Bali 42' catamaran, featuring exemplary amenities and an innovative spacious floor plan design.

  3. Key West Bareboat Charter

    You may also stay in Key West and take some day trips. Day charters aboard catamarans are available for reef snorkeling and sunset cruises. The high-speed ferry Yankee Freedom also leaves Key West daily at 8:00am to bring you to the Dry Tortugas. You'll be back by 5:00pm.

  4. 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.)

  5. Blue Ocean Yacht Charters

    Blue Ocean Yacht Charters, located in Key West, Florida, makes yacht rentals affordable and life-changing. We offer private multi-day bareboat charters to amazing destinations like The Dry Tortugas and the Florida Keys. Just looking for a day charter? Look no further. We offer four hour, eight hour, and 24 hour charters as well multi-day charters.

  6. Florida Bareboat & Captain Yacht Charters

    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 Crewed and Bareboat Charter, ASA Sailing Instruction and Yacht Management.

  7. Key West Bareboat Charters

    Looking for a bareboat charter for 6-12 guests in Key West, Florida? Casual Monday Charters has got you covered. Book Today! +1 305 988 1179 [email protected] ... your Key West Bareboat charter. • Hats • Beach towels • Sunscreen (please no spray on)

  8. Sailing Charters in Key Largo and Florida Keys

    Our bareboat charters offer you the chance to be in charge of a beautiful yacht and create your own rewarding sailing experience in an amazing location. Great planning is the key to making your charter special. We take great care in listening to your expectations so that we can come up with a charter tailor made for your cruising needs.

  9. Florida Keys Bareboat & Crewed Yacht Charters

    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 ...

  10. Luxury Catamaran Charter Key West

    It is so easy to reach the Florida Keys by direct domestic flights or by road trip, and the vibe and environment is much of what you find in foreign tropical vacation destinations. Experienced sailors with or without ASA certifications can qualify to bareboat with us and captain the catamaran on their own. We will review your sailing resume ...

  11. Sailing The Keys Sailboat Rental

    5 DAY BAREBOAT CRUISING OR 103 & 104. Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34. Offered all year on demand based on your travel plans. 5 Days and 4 Nights…Privately Living aboard at our Dock.

  12. Key West Sunset Sail Charters

    7005 Shrimp Road. Key West, FL 33040. 305-720-0896. Submit. Thanks for submitting! Book Now. Sail Away Key West is your source for the most luxurious private catamaran charters in Key West. We look forward to planning your customized itinerary so that we can share with you our passion for sailing as well as the stunning waters, reefs, and ...

  13. 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.

  14. 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 ...

  15. Key West Itineraries

    This charter lasts 4 hours from the time you cast off your lines from the dock until you return and may include fueling time. A suggested activity for this charter is to sail or motor to the coral reefs nearby (45-60 mins. one way), grab a mooring ball, and snorkel. Another activity would be to learn how to sail or drive the yacht.

  16. Florida Keys Yacht Charter

    Embark on a unique yacht charter adventure in Key West and the Dry Tortugas. Discover history, pristine natural beauty, and thrilling offshore passages. Yacht Warriors. Destinations ... Our 2021 Key West bareboat charter and sailing adventure to the Dry Tortugas. Great fishing, long passages, and plenty of history.

  17. Sailing Catamarans for Charter in Key West

    Explore our curated fleet of sailing catamarans available for bareboat charter, captain charter and ASA sailing instruction. ... Bali 4.2 Sailing Catamaran Key West 4 Cabins / 4 Baths / 2 Showers 8 Max Passengers (Including Captain & Crew) Details. Eeya.

  18. Key West Sailing

    We'll arrange everything: boat, captain and crew, and the best Key West sailing charter prices. Key West Florida is a historic seaport with a variety of daysailers for hire, as well as the bigger Key West yacht rentals. Take a 25-footer out for a full day or half-day trip around the island. Sail past Southernmost Point and see the world ...

  19. Sailing Yacht Charter Key West Sailboat Charters & Rentals

    Yacht Sun Odyssey 409 for rent in Key West. Sailing boat Rentals Key West › Oceanside Marina. Sailing boat - Sun Odyssey 409 - Built in: 2020 - Cabins: 2 - Berths: 4. Bareboat charter. Max 4 persons. The price is calculated for 7 day charter and 1 passenger. Price includes: Sun Odyssey 409 [Yacht Price incl. Taxes] Cockpit cushion.

  20. Key West Sailing Charters

    Step aboard one of our sailing monohulls in Key West for a bareboat charter, captain charter or ASA Sailing course. ... Bareboat Charter. Our Yachts. Sailing Catamarans. Sailing Monohulls. Destinations; Learn to Sail; Yacht Management; Request Quote; Sailing Monohulls TODscott 2024-06-30T15:00:09-04:00.

  21. Key West Yacht Charters in Florida: best fleet best deals

    Please request options and pricing that will best suit your needs and budget. We have many Fully Crewed All Inclusive options available! Tropical Yachts. 4906 N Travelers Palm Lane. Tamarac, FL 33319. Tel: 1 (305) 735-3460. E-mail: [email protected].

  22. Home Page

    Huntress also available for Sunset sails, Reef Trips, Day Sails and available for Bareboat Charters. Pricing: Overnight Stays / Bareboat Charters / Captained Charters: High Season: 450.00 per night / High Season: $5000.00 for 7 nights / Sunset Sail: $600.00. Low Season: $350.00 per night / Low Season: $3500.00 for 7 nights / Reef Trip: $1,200.00.

  23. Sailboat rental Key West with or without a skipper

    Nº1 Nº1 boat rental and yacht charter platform in United States. Choose from 2 Sailboats in Key West, United States starting from 838 € per day, with or without captain. ... Bareboat 2021 43 ft from 837 € SCHOONER AMERICA 105 Key West ...