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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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Discover your own holiday style. Browse and be inspired.

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

212 available holidays

Sailing holidays for fun addicted!

2 available holidays

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

4 available holidays

Top destinations.

Italy

174 holidays

Tuscany

54 holidays

Liguria

37 holidays

Aeolian Islands

25 holidays

Greece

7 holidays

Pontine Islands

5 holidays

Croatia

4 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

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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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