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Yacht sailing holidays & skippered tours in Guadeloupe

Discover hundreds of sailing holidays in Guadeloupe. Book a place on board and enjoy a unique experience with a local skipper with a local skipper at attractive prices.



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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 Guadeloupe

23 reviews

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Cruise around Guadeloupe


David H.


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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Cruise from Guadeloupe to Martinique


Daniele D.



Bellissima crociera, barca comoda e skipper impeccabile, grazie Jeanba!!!
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Cruise from Guadeloupe to Martinique


William B.



Je ne pouvais pas mieux tomber en premiere expérience de croisière dans les Antilles! Ce fut un séjour fantastique à tout point de vue. Jean Baptiste, un skipper vraiment hors pair qui sait s 'adapter à toutes les situations. Sécurité, convivialité, et découvertes. de sites magiques. Il m'a fait bénéficier de ses années de navigation sur les Caraibes à bord de son voilier sur et très confortable en. Une authentique expérience humaine à renouveler sans modération !
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Sailing in the French Creol


Hélène B.



J'ai reçu un très bon accueil du skipper Massimo et de sa compagne Sonia. Ils comprennent très bien le français. Les pâtes étaient excellentes. Massimo connait les meilleurs spots de snorking de la Guadeloupe. Le bateau est très confortable, propre et surtout sans odeur. La navigation était des plus agréables. J'ai hâte de découvrir d'autres îles avec eux.

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Guides & tips


From Cuba to the Grenadines, via the fascinating Bahamas and the green Antilles: Martinique, Dominica and Guadeloupe. Either way, a dream trip to tropical islands.
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