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Monohull yacht sailing holidays & tours in the Caribbean

Discover the magic of sailing holidays in the Caribbean! Monohull: a new way of traveling with your loved one, your friends or your family. Find your dream adventure among thousands of holidays from the Mediterranean to the Caribbeans.

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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 - Monohull yacht sailing holidays & tours in the Caribbean

79 reviews

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Paradise on a sailing boat with All Inclusive

07/19/2023

Liane F.

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Brazil

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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7 Days Sailing Cruise around St. Martin/St. Barth's/Anguilla incl. breakfast and lunch on board

03/28/2023

Thomas T.

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Austria

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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7 Days Sailing Cruise around St. Martin/St. Barth's/Anguilla incl. breakfast and lunch on board

03/27/2023

Emanuel R.

Wir haben uns rundum Wohl und Sicher gefühlt. Man kommt als Gast und geht als Teil der Familie. Auf unsere Wünsche wurde sowohl bei der Route als auch beim Essen eingegangen. Es ist eine Geschäftsbeziehung aber eine sehr angenehme, Danke für diese tolle Woche!
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Cruise around Guadeloupe

03/21/2023

David H.

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United States

My experience with Jean-Baptiste on Gibsea 52) in the cruise around Guadeloupe March 9 - 18was superlative! He and the boat flawlessly combined wonderful sailing with equally wonderful shore excursions based on his obvious extensive knowledge of the Islands (Guadeloupe, Les Saintes, Dominica, Marie Gallante) and surrounding waters. He was very helpful, courteous and patient in accommodating my particular travel needs from the US. And on that latter point his English is very good so I highly recommend him for those from the US like myself and other predominantly English-speaking places. Moreover he made it a point to translate other languages into English (but don't "hog" that as I tried not to and be respectful of other participants). Great cook too! In summation I had a wonderful time with Jean-Baptiste sailing, swimming, sunning and excursioning; would and hopefully will sail with him again; and recommend to the highest degree you do the same.

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