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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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4.3

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

5 departures available

August - September

Starting from

€1,250

€1,125

Per person - min 2 pax

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4.3

Premium

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

Caribbean: Grenadines & Martinique

9 days - 10 nights

3 departures available

August - September

Starting from

€1,680

€1,512

Per person - min 2 pax

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4.3

Premium

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

Caribbean: Saint Martin

6 days - 7 nights

3 departures available

August

Starting from

€1,205

€1,085

Per person - min 2 pax

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4.3

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GUADELOUPE Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Guadeloupe

6 days - 7 nights

3 departures available

August

Starting from

€1,125

€1,013

Per person - min 2 pax

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5.0

Discover Guadeloupe on a comfortable catamaran - All Inclusive

Caribbean: Guadeloupe

7 days - 7 nights

One departure available

August

Starting from

€1,272

Per person - min 2 pax

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4.3

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ABACO Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Bahamas

7 days - 7 nights

One departure available

August

Starting from

€1,885

€1,697

Per person - min 2 pax

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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

One departure available

August

Starting from

€1,500

€1,350

Per person

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4.3

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BVI TORTOLA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: BVI - British Virgin Islands

6 days - 7 nights

2 departures available

August

Starting from

€1,250

Per person - min 2 pax

Why book a holiday with Sailsquare?

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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 - Yacht sailing holidays & skippered tours in Caribbean

233 reviews

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Under the Caribbean sun on a catamaran

03/10/2026

Irene B.

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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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Four days in the paradise of the San Blas Islands - All inclusive

02/26/2026

Gianluca A.

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United States

Luigina and Alessandro made us feel at home since the very first moment. They cooked incredible meals, were always attentive to our needs, and we truly enjoyed spending time with them. It was probably one of our best family sailing adventures. On top of that they made us discover the San Blas islands: crystal clear water, white sand beaches, snorkeling, paddle boarding and of course sailing between the islands. So much to do and a joy doing it with them especially thanks to their deep knowledge of the are. Definitely highly recommended!!
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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

01/26/2026

Sabrina B.

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Italy

Fantastic experience and very qualified staff. Maybe I thought I would see more beaches but in general I was very satisfied.
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Unforgettable Mini Flotilla in the Caribbean - Dominica and Guadeloupe

01/26/2026

Giulia V.

-

Italy

Andrea and Federico are true professionals and always kind and very nice, capable and cheerful sailors, nautical experts and entertainers. Beautiful holiday, fun and in complete safety!

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