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Crewed yacht sailing holidays & tours in Caribbean

Discover more than 8 opportunities to get on board a Crewed adventure in Caribbean. A unique experience with a local skipper, starting at €350 a week.

8

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 - Crewed yacht sailing holidays & tours in Caribbean

41 reviews

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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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Dream Caribbean Premium - 11 days in catamaran ALL INCLUSIVE with hostess / cook

05/7/2023

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

03/30/2023

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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The Caribbean Dream with hostess & skipper

01/27/2023

Iordanka S.

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France

J’ai passé un séjour fabuleux dans les Caraïbes avec Dominikus et Patricia. Un régal autant pour les yeux que pour les papilles. Skipper et hôtesse incroyables, ils sont accueillants, compétents, très bien organisés et toujours aux petits soins pour nous. Au delà des paysages idylliques et eaux turquoises, c’est également un vrai plaisir de passer les soirées avec eux. Je recommande vivement l’expérience. Best life ever! Un grand merci pour tout! Iordanka

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