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Sport & wellness yacht sailing holidays & tours in Caribbean

Discover more than 1 opportunities to get on board a Sport & wellness adventure in Caribbean. A unique experience with a local skipper, starting at €350 a week.

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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 - Sport & wellness yacht sailing holidays & tours in Caribbean

29 reviews

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Wellness Adventure Retreat

01/14/2026

Donna S.

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Canada

We had an amazing time on board. Great food. Lots of activities. We got to see sharks, dolphins, and many types of tropical fish. Luca was a great host. The boat was beautiful and very clean. The location was absolutely stunning!
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Tobago Cays and Grenadines in Catamaran

09/26/2019

Lowijs S.

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France

That was my second time as crew member on Massimo's catamaean and we had an outstanding one week cruise in the Caribbean. Easy to go along with, Massimo is pretty good in finding the right spots for a relax mooring in a nice environment. It was a week in Paradise I'll never forget.
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Learning and relaxation in the Grenadines!

03/26/2019

Séverine B.

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France

A great trip with Hervé. Pedagogue, attentive, warm, a real pleasure to sail with him. We spent a heavenly week in the Grenadines Islands. Very good unforgettable moments dolphins, turtles, rays... lobster dinner... in short, to be done again very quickly Thank you Hervé
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Catamaran cruises in the Guadeloupean archipelago

03/10/2019

Eric F.

On est très en confiance avec Eric qui a une grande expérience de la mer sous tous ses aspects, y compris la course ! Il a un relationnel très sympa et franc. Pour ceux qui le veulent, apprentissage des manœuvres de base. Catamaran très spacieux et confortable : 3 cabines , chacune avec cOin toilettes + vaste cockpit pour les repas ou la détente. Sinon, songez que vous devez faire les courses et cuisiner et nettoyer/faire la vaisselle pour tous ! Les frais de repas, de port et de gazole sont en plus du prix payé ! Expérience très enrichissante de rencontres , d'humilité et de partage. Égoïstes et égocentriques : passez votre chemin ! Merci Eric pour cette passionnante aventure , une première pour nous. Et merci à Leila et Joseph, sympas viennois, compagnons de voyage idéaux. A bientôt !

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