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Yacht sailing holidays & skippered tours in Caribbean

Discover more than 7 sailing holidays in Caribbean. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

224 reviews

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

01/11/2026

Elena Maria F.

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Italy

The experience was wonderful. There were 2 inconveniences, the first was the wait in the port of departure of two guests who instead of arriving at 18.00 arrived at midnight and this led to a change of program on the first day, in fact we did not visit Bequia with Port Elizabeth at all. The second note is on the cook, who said she was at her first experience in that role and in the kitchen, in fact the management of the galley was bad. The dishes were too elaborate and used too many ingredients to the detriment of the quantities. After the middle of the week he realized that he could cook simpler and more abundant things. For the rest it was a wonderful experience.
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New Year's Eve Flotilla: 3 catamarans in the Caribbean

01/7/2026

Veronica M.

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Italy

As always, we feel like family, see you on the next adventure!
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Come and discover Guadeloupe and its archipelago: a paradise on the water

12/24/2025

Manfred B.

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Austria

It was a great week with Sabine and Patrick! They are very flexible and strive to accommodate every request! Every day a new adventure! Sailing, shore excursions, snorkeling......, - there is something for everyone
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Come and discover Guadeloupe and its archipelago: a paradise on the water

12/16/2025

Johannes T.

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Germany

That was a great, wonderful week. Many thanks to Sabine and Patrick! Best wishes Carola and Johannes

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