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Yacht sailing holidays & skippered tours in Caribbean

Discover more than 6 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

227 reviews

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New Year's Eve 2026 discovering the Lesser Antilles by catamaran

01/15/2026

Deborah C.

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Italy

Super-comfortable catamaran Itinerary definitely improvable Good organization Good skipper
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Wellness Adventure Retreat

01/14/2026

Donna S.

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Canada

We had an amazing time on board. Great food. Lots of activities. We got to see sharks, dolphins, and many types of tropical fish. Luca was a great host. The boat was beautiful and very clean. The location was absolutely stunning!
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Come and discover Guadeloupe and its archipelago: a paradise on the water

01/14/2026

Sophie P.

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Canada

An unforgettable sailing trip in Guadeloupe and the islands 🌴 We discovered Les Saintes, Marie-Galante and had a huge crush on Petite-Terre 💙 Sabrina and Patrick are incredibly welcoming and friendly. We spent a week on their sailboat, in a friendly and soothing atmosphere between tarot games and chili lovers and underwater excursions. 🌶️🃏 🐠 Patrick and Sabine are excellent skippers, very professional and reassuring. . This trip allowed us to really rest and recharge. An experience that I recommend without hesitation ✨ Sophie and Louis
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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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