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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.
Discover the other 743 holidays currently available!
Discover your own holiday style. Browse and be inspired.

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

6 available holidays

Sailing holidays for fun addicted!

3 available holidays

All-Inclusive sailing holidays: just relax and enjoy life onboard.

192 available holidays

Top destinations.

Italy

210 holidays

Tuscany

48 holidays

Liguria

40 holidays

Greece

25 holidays

Pontine Islands

20 holidays

Aeolian Islands

8 holidays

Croatia

6 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

1 holidays

Discover all destinations.
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5 Greek islands that few people know: discover them on a sailing boat!

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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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