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Yacht sailing holidays & skippered tours in Saint Martin

Discover more than 3 sailing holidays in Saint Martin. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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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 Saint Martin

9 reviews

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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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Caribbean sailing cruise in St. Martin - Anguilla

02/22/2020

Carla P.

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Italy

Francesco was replaced by Michele, maybe because of too much wind and the conditions of the sea but the holiday was a bed and breakfast anchored in Anguilla: no beach of st Marteen sight and not even of Anguilla.I had to organize the holidays on land and snorkelling in the beaches (alone) with extra costs for car and pastries on the beaches. Public Floor Shower at Sandy Ground... Back in St Marteen I discovered that the most beautiful bays were teeming with sailboats and catamarans!! So if there are extra costs for anchoring in Anguilla and stMarteen ok just specify it or increase the cost, but staying floating like a cork without moving is not a sailing holiday (I had specified that my only request was snorkelling) DO NOT BOOK IF THE ITINERARY IS NOT INDICATED even if only theoretical. I'm sorry because Michele is kind and cooks well, but the travel companion has catalyzed him a bit (and I don't know how reliable as an assistant skipper) It remains my worst holiday

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