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Private yacht sailing holidays with skipper in the Caribbean

Discover the magic of sailing holidays in the Caribbeans! Renting a sailing boat: a new way of traveling with your loved one, your friends or your family. Find your dream adventure among hundreds of holidays organised by local skippers.

Why book a holiday with Sailsquare?

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The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Private yacht sailing holidays with skipper in the Caribbean

11 reviews

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Under the Caribbean sun on a catamaran

03/10/2026

Irene B.

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Italy

The boat is very beautiful, well maintained and equipped with many comforts, and this makes your stay on board pleasant. The itinerary is also interesting, but with elements to take into consideration: several hours of navigation are planned (about 12 on the first day and 6 on the second, as well as similar times in the last days of return). In addition, these are areas where, once you arrive in the evening, it is not always easy to experience the place: many merchants close as early as around 9 pm, so the opportunities to explore on land are limited. The crew proved to be competent and attentive to the safety of navigation, with attention to detail during meals and attention to everyone's dietary needs. However, in general, it would have been appreciable to have more involvement of guests in the small choices of the week (such as the organization of the day and activities). A more proactive approach to sharing information and opportunities would have made the experience even more enjoyable and participatory. The same principle would also apply to the management of the common fund (€ 600 per person), of which we did not have visibility during the week. An episode related to the blockage of the toilet was also handled in disrespectful tones and with an immediate attribution of responsibility, before the technical cause of the problem was clarified. The solution was to use the bathroom of the other guests, which was only made possible thanks to the climate of collaboration between us participants. Again, a more balanced approach to managing the situation would certainly have been appreciated. Overall, an experience with several positive aspects, but with some room for improvement in the management of communication and relationship with guests.
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Come and discover Guadeloupe and its archipelago: a paradise on the water

01/14/2026

Sophie P.

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Canada

An unforgettable sailing trip in Guadeloupe and the islands 🌴 We discovered Les Saintes, Marie-Galante and had a huge crush on Petite-Terre 💙 Sabrina and Patrick are incredibly welcoming and friendly. We spent a week on their sailboat, in a friendly and soothing atmosphere between tarot games and chili lovers and underwater excursions. 🌶️🃏 🐠 Patrick and Sabine are excellent skippers, very professional and reassuring. . This trip allowed us to really rest and recharge. An experience that I recommend without hesitation ✨ Sophie and Louis
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Come and discover Guadeloupe and its archipelago: a paradise on the water

12/24/2025

Manfred B.

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Austria

It was a great week with Sabine and Patrick! They are very flexible and strive to accommodate every request! Every day a new adventure! Sailing, shore excursions, snorkeling......, - there is something for everyone
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Come and discover Guadeloupe and its archipelago: a paradise on the water

12/16/2025

Johannes T.

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Germany

That was a great, wonderful week. Many thanks to Sabine and Patrick! Best wishes Carola and Johannes

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6 reasons to charter a Caribbean yacht:

  • Enjoy a week of summer during the winter on a Caribbean yacht charter Sailboat in the Caribbean
  • Discover paradisiacal beaches, swim in crystal clear waters and relax under palm trees, away from the tourist crowds
  • Take the Caribbean yacht charter and learn from your skipper during a sailing course
  • Enjoy the comfort and space aboard a sailing yacht or catamaran with your loved ones
  • Rent a catamaran in the Caribbean and enjoy an unforgettable experience on board
  • Sail or catamaran sail with a local skipper and immerse yourself in the culture of your holiday destination

Advantages of yacht charter in the Caribbean:

Caribbean Sailing Yacht Charter

Sailboat charter in the Caribbean is the perfect way to have a great time with family or with a group of friends. Plan your sailing route with your local skipper and enjoy a unique and personalised experience. Your skipper will know how to recommend the most beautiful beaches and the most remote islands to make your dream sailing holiday come true.

Catamaran charter in the Caribbean

Especially in the Caribbean, it's wise to consider chartering a catamaran. In the often shallow waters, a catamaran will allow you to sail smoothly, as it is shallower in the water. Catamaran sailing also means luxury and plenty of space: relax on deck, sleep under the stars on the catamaran's net and discover the breathtaking scenery of the Caribbean.

Everything you need to know about chartering a Caribbean boat:

  • We recommend planning a Caribbean yacht charter in November, February and March, so you can avoid the high season and tourist crowds. Travel to the Caribbean between late May and early November should be avoided as there is an increased risk of hurricanes during this period.
  • The Caribbean is ideal for a relaxing holiday with your family, but a Caribbean yacht charter with friends is also very popular. Choose the experience that best suits your needs from a wide range of offers and enjoy an unforgettable holiday.
  • It's always advisable to plan a two-week holiday to really enjoy the trip and discover all the wonderful places in the area at your leisure.
  • Many Caribbean islands have good connections via international airports and some islands have direct flights from Europe.

The best itineraries for Caribbean yacht charter:

Some examples of itineraries:

  • Route through Bahamas: Marsh Harbour - Elbow Cay - Man O War Cay - Green Turtle Cay - Treasure Cay - Marsh Harbour.
  • Route through Cuba: Cienfuegos - Tiki Bay of Pigs - Isle of Youth - National Park - Cayo Largo - Trinidad - Cayo Cinco Balas - Rancho Luca Beach - Cienfuegos

Caribbean: the best travel ideas

Other travel ideas

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