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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 708 holidays currently available!

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

137 available holidays

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

88 available holidays

Discover real nature on a sailboat.

255 available holidays

Discover your own holiday style. Browse and be inspired.

Top destinations.

Tuscany

55 holidays

Italy

209 holidays

Liguria

44 holidays

Pontine Islands

34 holidays

Aeolian Islands

4 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

2 holidays

Caribbean

112 holidays

Aegadian islands

11 holidays

Discover all destinations.
from the blog

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 travelers.

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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