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Choose your sailing holiday among thousands of unique experiences.

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Not just sailing: adventure travel and more, for all tastes. Browse all experiences

Discover your own holiday style. Browse and be inspired.

Top destinations.

France

210 holidays

Caribbean

179 holidays

Italy

158 holidays

Canary Islands

71 holidays

Liguria

18 holidays

Tuscany

51 holidays

Greece

70 holidays

Balearic Islands

68 holidays

from the blog

Questions, doubts and interesting facts for sailing boat beginners

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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.

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

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