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Choose your sailing holiday among thousands of unique experiences.

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Travel alone or in a group and meet new sailing friends.
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All-Inclusive sailing holidays: just relax and enjoy life onboard.

108 available holidays

Sailing holidays for fun addicted!

63 available holidays

Wishing for a sailing holiday with your family? Time to make your dream come true.

136 available holidays
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Top destinations.

Italy

1297 holidays

Greece

490 holidays

Corsica

268 holidays

Aeolian Islands

227 holidays

Tuscany

272 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

189 holidays

Liguria

119 holidays

Pontine Islands

130 holidays

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Sailsquare is the ultimate connection between skippers and travellers.

Skippers create holidays following their passions, the others will simply enjoy an unforgettable holiday.

Discover who is already on board before you leave!

Meet on Sailsquare, get to know each other on the boat and go home with new friends.

We're here to help before, after or during the holiday

You can contact our customer care or your skipper directly. We're here for you!

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