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Holidays and Sailing Cruises by Sailboat and Catamaran in Saint Martin

Set off on the sailing cruise of your dreams to discover the pearl of the Caribbean. Treat yourself to a holiday among hidden bays, colorful markets, and Caribbean rhythms. Golden sandy beaches, turquoise waters, breathtaking views, and steady winds await you — perfect for experiencing this paradise under sail.

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 - Holidays and Sailing Cruises by Sailboat and Catamaran in Saint Martin

10 reviews

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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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12 day Cruising/Sailing Experience around St. Martin and St. Barth's

04/17/2025

Basiel B.

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United States

We had a fantastic trip sailing around St. Martin, St. Barth and St. Kitts & Nevis with Rob and Jackie, who were super relaxed and made us feel 200% welcome. The boat is beautiful and very well taken care of, a perfect intro to real-deal sailing. Rob is an excellent skipper mindful of safety (& comfort), and Jackie spoils you with her cooking. Snorkeling gear an paddle board available for aquatic leisure. Cannot recommend them more for a relaxing trip around the Caribbean!
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7 Days Sailing Cruise around St. Martin/St. Barth's/Anguilla incl. breakfast and lunch on board

03/28/2023

Thomas T.

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Austria

On the --- everyone gets their money's worth, whether you just want to relax and relax, or join in the sailing, everything is possible. You can learn a lot from Rob the old sea dog and draw on his wealth of experience. Jacky, on the other hand, pampers you from front to back and lets you enjoy many delicacies. The two radiate such a calmness that you feel safe with them. Thanks again for everything!
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7 Days Sailing Cruise around St. Martin/St. Barth's/Anguilla incl. breakfast and lunch on board

03/27/2023

Emanuel R.

We felt completely comfortable and safe. You come as a guest and leave as part of the family. Our wishes were taken into account both in the route and in the food. It's a business relationship but a very pleasant one, thank you for this great week!

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