The Caribbean is a premier yachting destination and boasts many romantic weekend getaways, with 700 tropical islands to discover. The warm climate and beautiful waters are top draws for many sailing enthusiasts. With all-inclusive resorts, rustic beachfront towns, popular beaches, and deserted islands, the region offers plenty of sun, sand, and sea for all vacationers. It consists of the Bahamas, Bermuda, Cayman Islands, Cuba, Jamaica, Haiti, Dominican Republic, Puerto Rico, Turks and Caicos Islands, as well as the Greater and Lesser Antilles chain of islands. The islands are rich in history and culture, which are reflected in different kinds of dishes that have influences from English, Spanish, French, Dutch, and African cuisines. Uncover endless wonders by sailing. Read on for more information on the top yacht charters in the Caribbean.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 24, 2025.
1. Serene boat with interior adorned with beautiful wooden accents (from USD 150)
Welcome aboard this extraordinary vessel, where you’ll discover a cosy interior adorned with beautiful wooden accents. It’s the ideal spot for two adults and two kids, boasting fully equipped facilities, a kitchen, and a living area. Set the mood with your favourite tunes via the Bluetooth speaker and relish the comfort of life on board.
The marina offers all the conveniences you need, from shops to a diving club and hot showers. Right across the street, there’s a delightful musical bar waiting for you. Take a leisurely 2-minute stroll to the beach or consider an exciting day trip (extra cost) to Saints and Leeward. Keep in mind, the boat’s lack of shutters adds to the adventurous charm of your stay.
Gourbeyre, Basse-Terre, GuadeloupeSuperhost
Accommodates: 2
2. Cosy sailboat with sailing lessons and snorkelling escapades (from USD 60)
Step aboard and be captivated by the mesmerizing seascape as their skilled captain navigates the azure waters. Their vessel offers all the comforts you need, with a well-equipped kitchen for delightful onboard dining and high-speed Wi-Fi to stay connected. Immerse yourself in harmonious melodies through their premium sound system and enjoy the elegant interior, featuring a cosy bath and shower for your ultimate comfort. Wake up to a sumptuous breakfast prepared just for you.
If you’re up for more adventure, set sail to the enchanting Saona or Catalina islands for a small fee (100$), relishing three delicious meals daily. After 4 pm, enjoy the seclusion and create unforgettable memories. Thrill-seekers can also join sailing lessons and snorkelling escapades, with top-notch gear provided for your enjoyment.
Ocho Rios, JamaicaAccommodates: 6
Top guest reviews
Host:
he's also a lovely host to spend time withcharlie is a super host the boat is amazing and the experience is fabulous i really recommend ithe taught us a lot about sailing and shared his experiences in the area which was very helpfulfor a different kind of experience i recommend staying on charlie's boatcharlie and alexandra are wonderful hosts the sailboat excursion was an adventure we won’t forgetCleanliness:
bed sheets and towels are cleanRead more reviewsAmenities & Room:
if you are tall make sure your measurements fit into the bedroom ( and the toilet/shower room)
3. Beautiful catamaran with an "All In Discovery" pass in Saint Barthélemy
Discover the beautiful islands and coastlines of the Caribbean by renting this double-hulled catamaran that can accommodate up to five guests. The two affable hosts are happy to bring you and your friends for a cruise around the island of St. Barth’s and beyond, with the “All In Discovery” pass that includes all food, drinks, fuel, and harbour dues.
Families with children will love to know that children will get to come onboard for a fun-filled vacation, at a special price.
Accommodates: 7
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Read more reviewsHost:
they were gracious hosts and wanted us to make their home our home
4. Lovely yacht with an experienced captain in the Bahamas
Go on an adventure of a lifetime with a captain who has more than four decades of sailing experience around the Caribbean. Setting off from Cat Island, this yacht rental in the Caribbean comes with a gracious captain who is happy to lead a sailing trip and accommodate your wishes as much as possible. While you discover unspoiled islands, deserted beaches, mangrove habitats or splash around in the turquoise waters, the captain will not only ensure a safe and memorable vacation but will also cook all meals on board and provide sailing tips for those who are keen to learn.
Stand-up paddle boards and fishing gear are also included in the charter.
CAT ISLAND, Cat Island, Bahamas
Top guest reviews
Host:
We also caught some fish had sushi and fabulous sundowners with live musicWhat an amazing experience to sail with Dave CalvertMy family and I had the most memorable couple of days on the beautiful DestinyHis wife is a great cook and is always got a smile onWe raced sailboards together while traveling around the USLocation:
Definitely one of my best sailing experiences and keeping memories for a lifetimegoing snorkeling or paddle boarding or just riding the dinghy to a hidden channel in the mangrove and discovering the area is a real treatThe meals were well prepared especially the fresh caught tuna and lobster Be sure to visit Conception Island National Park to see the green turtles in Conception CreekI had never been on a boat like that it really was an experience I want to repeatRead more reviewsAmenities & Room:
Dave is an expert sailor as mentioned in other reviewsI've known Dave Calvert for over 40 years
5. Homey yacht with water sports gear in St. Thomas
Step on board the “Guiding Light,” a homey and spacious yacht in St. Thomas, the U.S. Virgin Islands, and start your adventure in the Caribbean Sea. The captain customises each trip according to your preferences and offers many ideas and cruising options that he will be happy to share. He is also a great cook and an entertaining host.
There are loads of water sports gear on board the catamaran for guests’ use, and there will be a lot of islands in the Caribbean to explore. All you have to do is bring your swimsuit, sunscreen, and sense of adventure.
Accommodates: 6
Minimum Nights: 5
Refund Policy :
Top guest reviews
Cleanliness:
shane is delightful clean cut and funour clean and cozy quarters were comfortable at night with plenty of ocean breezethe boat was beautiful sparkling clean and exceedingly comfortableRead more reviewsAmenities & Room:
the accommodations were comfortable- good sleeping with the breeze and rocking boat
6. Luxurious boat with sailing options in the British Virgin Islands
Delve into tales of ocean adventures and the thrills of being a yachtie with the hosts on board “Alexis3,” a luxurious catamaran. This luxury yacht charter in the Caribbean departs from the British Virgin Islands, and it is captained by a couple. One of your hosts can prepare scrumptious meals for you.
There are many sailing options available that come with different pricing structures, so do discuss your preferences with the hosts. Whatever it is you decide, rest assured that you will be having a glorious vacation on board a beautiful boat for the most memorable trip of a lifetime.
Accommodates: 6
Minimum Nights: 5
Refund Policy :
Top guest reviews
Host:
i had the privilege to spent my time in the bvi"s with theo and gussie as my hostsi just want to personally thank theo and gussie for being the best host and hostessRead more reviewsCleanliness:
the boat was very clean and spacious and we did not feel on top of each other
7. Classy catamaran with four cabins in St. Thomas
“Eclipse” is a classy catamaran that sets sail from St. Thomas in the U.S. Virgin Islands. It exudes luxury, from bow to stern. It has wide spaces that are all perfectly appointed for guests. There are four guest cabins with ensuite bathrooms and air conditioning. The hosts are incredibly experienced, and you can expect minimum fuss and maximum pampering during your Caribbean vacation.
Accommodates: 8
Minimum Nights: 6
Refund Policy :
Top guest reviews
Host:
her friendly and bubbly personality made us feel at homeRead more reviewsAmenities & Room:
it's huge comfortable and perfect for our group of 8
8. Pretty yacht with meals and drinks in St. Thomas
On board the “Vivo,” you will get to enjoy your vacation in the Caribbean Sea. The captain and crew will ensure your stay is a memorable one. You will depart from St. Thomas in the U.S. Virgin Islands and start exploring the beautiful Caribbean and its many islands and clear waters. Meals, drinks, and water sports toys are provided. All you need to do is sit back and let the warm breeze carry your worries away.
st thomas, st thomas, U.S. Virgin Islands
9. Fantastic sailboat with water sports toys in St. Thomas
Set sail from St. Thomas in the U.S. Virgin Islands with this “Purple Pelican,” a roomy sailboat hosted by a captain who is a USCG certified captain and first Mate. The captain is also a certified culinary chef. This sailboat rental in the Caribbean comes with an assortment of water sports toys, so you will have many fun-filled hours on the water.
You will get to wake up to a different scenery each day and explore secret coves and deserted beaches. You will also experience first-rate hospitality during your memorable trip.
St Thomas, St Thomas, U.S. Virgin Islands
Top guest reviews
Read more reviewsCleanliness:
they’re passion for the purple pelican shows and it’s impeccably clean and comfortable
10. Gorgeous sailboat for day cruises in Saint Martin
Based in Marigot in St. Martin, this sailboat and its captain offer cruises around Saint Martin, Anguilla, and St. Barts for up to four guests for the ultimate sailing adventure. There are also options to just stay on board the yacht while it is docked and go on day and sunset cruises. The best option is to entrust yourselves in the capable hands of the captain and just go on an adventure to discover the best-kept secrets of Saint Martin.
Marigot, Collectivité de Saint-Martin, Saint Martin
Top guest reviews
Host:
the owner was an extremely exceptional hosthad our very first sailing adventure withWe enjoyed our chats with Alex and are so thankful for all he did to make our stay truly enjoyableHe knew where to go what to see and how to best experience many beautiful and authentic locations in St Martin AnguillaSailing was peaceful and restorative to the soulLocation:
We have memories to last a life timeThis can be a great relaxing way to begin a vacation after a long flightRead more reviewsAmenities & Room:
Alex is an experienced sailor and savvy cook tooOur family of 4 (two children aged 2 and 4 plus mom and dad)
11. Unique boat at a high-end marina in St. Lucia
If you have never experienced staying on a yacht or at a first-rate marina, then this sailboat is a great introduction into that lifestyle. “YOTA” is a boat docked at Rodney Bay Marina in St. Lucia. This high-end marina offers all the conveniences of a resort, including a swimming pool, shops, cafes, and restaurants.
The yacht has cabins that are perfect for a small family getaway. The host can organise day and sunset cruises around St. Lucia and beyond, so do enquire to find out more.
gros islet, Gros Islet, Saint Lucia
Top guest reviews
Read more reviewsAmenities & Room:
the bedrooms (4 total) are cozy and comfortable with room to stand
Sail through the Caribbean
There is no better backdrop for a sailing adventure than the beautiful Caribbean. Warm sea breezes and pristine waters beckon all sun seekers to the many islands and beaches. For the uninitiated or the experienced seafarer, the Caribbean never ceases to amaze. Add this region on your bucket list and set sail with one of the best catamaran charters in the Caribbean.
Frequently asked questions about yacht charters in the Caribbean
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data