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Top destinations.

Italy

204 holidays

Tuscany

60 holidays

Liguria

39 holidays

Aeolian Islands

38 holidays

Pontine Islands

9 holidays

Greece

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Croatia

4 holidays

from the blog

Sailing holidays: embrace a peaceful state of mind

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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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