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Yacht sailing holidays & skippered tours in Caribbean

Discover more than 9 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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4.4

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

5 departures available

November - December

Starting from

€1,385

€1,108

Per person - min 2 pax

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4.4

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ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Saint Martin

6 days - 7 nights

3 departures available

November - December

Starting from

€1,205

€1,085

Per person - min 2 pax

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4.4

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GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

9 days - 10 nights

2 departures available

December

Starting from

€1,680

€1,512

Per person - min 2 pax

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4.4

Atlantic crossing by sailboat from Tenerife to the Caribbean

Caribbean: Grenadines & Martinique

20 days - 20 nights

One departure available

November - December

€3,900

Per person

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4.4

New Year's Eve in the Caribbean: Martinique and the Grenadines OneWay

Caribbean: Grenadines & Martinique

10 days - 11 nights

One departure available

December - January

€1,590

Per person

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4.4

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GUADELOUPE Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Guadeloupe

6 days - 7 nights

3 departures available

November - December

Starting from

€1,125

€1,013

Per person - min 2 pax

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4.4

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BAHAMAS EXUMA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Bahamas

6 days - 7 nights

3 departures available

November - December

Starting from

€1,940

Per person

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5.0

A dream trip for 2 people in the wilderness - All inclusive

Caribbean: San Blas Islands - Panama

6 days - 6 nights

4 departures available

November - December

Starting from

€1,500

Per person

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4.4

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BVI TORTOLA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: BVI - British Virgin Islands

6 days - 7 nights

3 departures available

November - December

Starting from

€1,250

Per person - min 2 pax

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Reviews - Yacht sailing holidays & skippered tours in Caribbean

239 reviews

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

05/18/2026

David B.

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Martinique

Amazing week in the Grenadines. Great group for the boat. A big thank you to the Skipper, Will and the hostess Maîka who prepared delicious meals for us. It was a perfect week for me. I recommend.

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

05/9/2026

Giorgia P.

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Italy

Very nice catamaran even if there were not enough bottles of wine on board among those we requested. Skipper good but preferred to speak in French and often did not adapt to the requests of us passengers. Nice itinerary but there is not much coral reef and fish, compared to other destinations. Very long crossings between one island and another and with always very rough seas.
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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

05/4/2026

Anna Maria M.

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Italy

A week based entirely on navigation, with little time for snorkeling. Obligatory, prepaid shore trips that were worth just a great lobster lunch on the beach. Rigid aperitif times, lunch and dinner, inflexible cook on the menu chosen at his unquestionable will. No possibility of changing the menu of the day, because it was not declared before and therefore sometimes we were left without being able to eat. Tense atmosphere if you didn't like the food or had requests, also due to linguistic misunderstanding. The crew spoke only French, no English or little. The quality of the wine and food is low. Frozen fish in bags, except on the first day. Cocktails that are good only on two or three occasions, because they are freshly prepared. For the rest, bottles of rum and fruit already prepared and hot. Disappointing holiday despite the very beautiful location.

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

05/3/2026

Michela T.

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Italy

The boat was very nice but I found the rules on board too strict, for example lunch at 12 and dinner at 19 for an all-Italian crew it is too early and we would have liked more flexibility. In addition, the language on board was French and, fortunately, English. Too little for an international cruise.

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