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Choose your sailing holiday among thousands of unique experiences.

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Top destinations.

Greece

322 holidays

Italy

784 holidays

Aeolian Islands

156 holidays

Croatia

118 holidays

Balearic Islands

143 holidays

Tuscany

161 holidays

Cyclades

70 holidays

Liguria

72 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.

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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