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Yacht sailing holidays & skippered tours in the Caribbean

Discover the magic of sailing holidays in the Caribbean! Get on board with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture and gastronomy.



Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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 - Yacht sailing holidays & skippered tours in the Caribbean

172 reviews

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Paradise on a sailing boat with All Inclusive


Liane F.



Wonderful week!!!! I recommend for everyone who loves sea, hot temperatures, piece, relax , nature. Mira is fantastic, excellent company, cooks very well, makes you feel comfortable, excellent skyper!!! Congratulations ???????? San blas, is A place to be visit . The best way is to be in sailing boat. Don’t loose it, you will never forget!!!! Thank you Mira for all nice days ????????????????????
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Dream Caribbean Premium - 11 days in catamaran ALL INCLUSIVE with hostess / cook


Rob H.

Stunning trip - wonderful deserted beaches, incredible snorkling (though sad that the coral is so depleted), and delicious food. Skipper was Eric and Yuna i.c. the kitchen.
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EXUMA Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook


Gianluca C.

Esperienze nel complesso ottima ,equipaggio gentile e capace ,skipper espertissimo,livello del cibo e preparazione ottima . Tutto ha funzionato senza intoppi ,per l accoglienza consiglierei hai non esperti di farsi organizzare accompagnamento dall' aeroporto. Stagione non fortunatissima ma nel complesso non male posti molto belli non adatti alla pesca ,mare splendido ,esperienza positiva
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7 Days Sailing Cruise around St. Martin/St. Barth's/Anguilla incl. breakfast and lunch on board


Thomas T.



Auf der --- kommt jeder auf seine Kosten, ob man einfach mal die Seele baumeln lassen und nur entspannen, oder beim Segeln ein wenig mitmachen möchte, alles ist möglich. Von Rob dem alten Seebären kann man viel lernen und aus seinem reichen Erfahrungsschatz schöpfen. Jacky hingegen verwöhnt einem von vorne bis hinten und lässt einem viele Köstlichkeiten genießen. Die beiden strahlen so eine Ruhe aus, dass man sich bei ihnen geborgen fühlt. Danke noch einmal für alles!

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Guides & tips


From Cuba to the Grenadines, via the fascinating Bahamas and the green Antilles: Martinique, Dominica and Guadeloupe. Either way, a dream trip to tropical islands.
Guide to the Caribbean by catamaran

When to go in the Caribbean

What are the best times to go to the Caribbean? What climate will I find?
Caribbean weather and climate guide

British Virgin Islands

Crystal-clear waters, rich seabed, lush vegetation and expanses of white sand are the main features of this paradise, which is a must-visit aboard a sailboat!
Guide to the BVI's by catamaran


Une constellation d'îles immergées dans une mer cristalline allant du vert au bleu profond : les fonds marins limpides cachent un trésor qui n'est pas seulement celui des pirates..
Guide to the Grenadines by catamaran


Un voyage en catamaran aux Bahamas est une expérience extraordinaire qui mêle aventure et détente au sein d'un incroyable patrimoine naturel.
Guide to the Bahamas by catamaran

Caribbean: the most beautiful places to sail

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