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Yacht sailing holidays & skippered tours in Caribbean

Discover more than 5 sailing holidays in Caribbean. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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experiences

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 Caribbean

205 reviews

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Guadeloupe and its islands in ten days

02/10/2024

Caterina P.

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Italy

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

02/9/2024

Franck P.

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France

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

02/8/2024

Lucie C.

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France

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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Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook

02/5/2024

MARIO I.

when I made the reservation I paid for a superior cabin and with the specific request written to you to have a bow cabin. I was assigned a central cabin, I would have liked an official communication from you, informing me of the availability or otherwise of the forward cabin and leaving me the free will to decide whether to accept or not, or withdraw from the contract for which I had paid. commercial and communication incorrectness

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