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Yacht sailing holidays & skippered tours in Caribbean

Discover more than 8 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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4.5

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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

€1,250

€1,125

Per person - min 2 pax

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4.5

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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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4.5

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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

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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4.5

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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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4.5

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ABACO Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Bahamas

7 days - 7 nights

3 departures available

November - December

Starting from

€1,885

€1,697

Per person - min 2 pax

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4.5

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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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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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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 Caribbean

235 reviews

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

04/16/2026

DONATELLA D.

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Italy

My rating is just enough and I would actually only give it 2 stars. Unfortunately the holiday turned out to be far below expectations, the quality / price ratio is very bad. First of all, the French skipper who speaks almost no English is unacceptable with a group of guests from various nationalities. In case of emergency, the captain must know how to give clear and quick orders and he would not have been able at all. The French hostess (his girlfriend) cooked everything except "navigation" food: for the whole holiday as vegetables only two salad leaves and one evening green beans, in the first three days there was practically no fruit and in the tropics it is a must, fish eaten only twice and meat after all; he always cooked heavy lunches / dinners that did not go well with the environment and the temperature ... The answers to the various intolerances or requests for vegetarian dishes were rude and considered only sometimes. The group we sailed with fortunately turned out to be the trump card of the holiday, we were all on the same wavelength and complained about the same things. Our collective requests to stay a little longer in one place or to change times for activities have never been answered in the affirmative, revealing an excessive rigidity on the program and on the needs of the captain-hostess as a couple. Another sore point is navigation: 13 hours at night as soon as you embark and then immediately "segregated" in the cabin with the order not to leave until 6 in the morning is madness. In our group two people were sick, one of whom was in a single cabin and neither the hostess nor the captain bothered to go and check on her and give her a hand in case of need. Unfortunately, even the places visited are below expectations: obviously they are beautiful places, but as far as coral reefs and marine fauna are concerned, they are very lacking. They made us do 2-3 snorkeling in very busy places (a little bit for a week on the boat). The cleanliness left a bit to be desired and note that the cabin has to be cleaned by itself throughout the week. Basically I loved the catamaran and the holiday at sea but there were too many poor points so in the future I will definitely evaluate other destinations and modalities.
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ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

04/3/2026

gulce c.

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Türkiye

It was wonderful, thank you !
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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

03/31/2026

Roberto C.

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Italy

An unforgettable experience thanks also to the whole team, both organizational and on the boat. Highly recommended tour, perhaps to be tackled with a few more days on the boat to avoid long crossings back.
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Under the Caribbean sun on a catamaran

03/10/2026

Irene B.

-

Italy

The boat is very beautiful, well maintained and equipped with many comforts, and this makes your stay on board pleasant. The itinerary is also interesting, but with elements to take into consideration: several hours of navigation are planned (about 12 on the first day and 6 on the second, as well as similar times in the last days of return). In addition, these are areas where, once you arrive in the evening, it is not always easy to experience the place: many merchants close as early as around 9 pm, so the opportunities to explore on land are limited. The crew proved to be competent and attentive to the safety of navigation, with attention to detail during meals and attention to everyone's dietary needs. However, in general, it would have been appreciable to have more involvement of guests in the small choices of the week (such as the organization of the day and activities). A more proactive approach to sharing information and opportunities would have made the experience even more enjoyable and participatory. The same principle would also apply to the management of the common fund (€ 600 per person), of which we did not have visibility during the week. An episode related to the blockage of the toilet was also handled in disrespectful tones and with an immediate attribution of responsibility, before the technical cause of the problem was clarified. The solution was to use the bathroom of the other guests, which was only made possible thanks to the climate of collaboration between us participants. Again, a more balanced approach to managing the situation would certainly have been appreciated. Overall, an experience with several positive aspects, but with some room for improvement in the management of communication and relationship with guests.

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