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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.



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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

5 reviews

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Guadeloupe and its islands in ten days


Caterina P.



At first, from my son Guglielmo , a special thanks to J.B. for his prompt interest and kind concern when we had problems to get in touch because of my smartphone (next time better an e sim). Than, even if i'm not exactly the best guest to have on bord, i received any kind of support to make me feel confortable and enjoy my stay.. You'll find someone who loves his job and who knows how to do it at best. Really good experience thanks also to Adriana, LuLu e Franco. See you soon!
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Guadeloupe and its islands in ten days


Franck P.



J’ai passé un super séjour sur le Mango qui est un voilier de voyage hyper abouti. Des vrais sensations de Voile…..! Merci à Jean Baptiste pour son accueil authentique qui aime partager ces connaissances et qui m a fait les beaux sites traversés…. À très bientôt. Franck
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Guadeloupe and its islands in ten days


Lucie C.



Super accueil. Jean Baptiste est très agréable très professionnel et surtout très securisant en.mer. il connaît son bateau dans tous les détails. Très bon séjour avec une bonne ambiance. Jean Baptiste nous a fait decouvrir de très beaux endroits. . nous le recommandons vivement. Adriana Lucie et Franck
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Martinique / Marie-Galante / Les Saintes / Martinique - 9 days sailing course, 250 NM


Fabien B.



Bellissima giornata!!! Ottima ospitalità di Marco e sua moglie!! Alla prossima

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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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