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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

28 reviews

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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

Un super voyage avec Hervé. Pédagogue, attentif, chaleureux, un vrai plaisir de naviguer avec lui. Nous avons passé une semaine paradisiaque dans les îles grenadines. De très bons moments inoubliables dauphins, tortues, raies...dîner aux langoustes...bref à refaire très vite Merci 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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Crociera di kitesurf nelle Grenadine

02/21/2019

Anne-Florence P.

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Guadeloupe

On D2 of the cruise in the canal connecting St Lucia to St Vincent, the autopilot of our boat (our skipper being busy as every day smoking and looking for network on his phone) was surprised by a huge wave laying the boat and throwing me from one side of the boat to the other. Fortunately, I was thrown on metal bars and not in the water in rough seas, causing only multiple bruises and contractures and not drowning. Derogatory and incessant remarks about the storage of dishes, the use of light; non-functional shower; the continuous bad mood of the skipper; his lack of knowledge of kitesurfing spots during a kite cruise only degraded a cruise already badly started. To top off this trip, the skipper made a scene because we had paid him many of his cocktails but no restaurant. Only positive point, Fred cooks properly.

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