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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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Reviews - Yacht sailing holidays & skippered tours in Caribbean

245 reviews

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

09/7/2026

GURMEET S.

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US

Sailing around Martinique, St Vincent and the Grenadines, was spectacular, with excursions for a small fee highly memorable. The skipper Gerard was extremely professional, skilled, providing a smooth, flawless sail on a 54 foot, high quality, well equipped catamaran with very comfortable cabins. This experience could easily have been a 5 star rating, were it not for the one crew member dedicated to general guest services and cuisine on board. Dream Yacht Charter employed someone lacking the minimum professional skills one would expect in the hospitality sector. The crew member had an indolent, disinterested and shoddy attitude, leaving guests feeling like a cumbersome burden. Simply asking politely for extra utensils or plates at meal times was met with scowls and complaints about extra washing up! The lack of hygiene on board was also unacceptable with whatever dirt that accumulated over the week inside the cabins and common areas building up. The kitchen was only superficially cleaned and on more than one occasion left flies and insects to fester. Cuisine cooked on board was generally flavourless, uninspired and even insufficient on occasion. This was frustrating when the program is full board for the week. We have travelled on other vessels with other companies and had a far better level of service for similar cost. All that said, we had a wonderful week sailing, we just would not book with this company again.
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ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

08/24/2026

Barbara R.

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IT

5 stars for this trip that fully met expectations, Comfortable boat, prepared and professional crew but at the same time friendly and attentive to everyone's needs. Well thought out itinerary with the right mix of activities and relaxation. The islands are beautiful with beautiful beaches!
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BVI TORTOLA Paradise - Catamaran cruise with hostess FULL BOARD

08/9/2026

Julie H.

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GB

Living like a millionaire, spending allot less than a resort!!! FABULOUS!!!! Best vacation ever!
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GUADELOUPE Paradise - Catamaran cruise with hostess FULL BOARD

08/5/2026

Maike H.

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CH

Bernard and Stéfanie were great. The trip was really nice and relaxing, exactly what I had been hoping for.

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