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Choose your sailing holiday among thousands of unique experiences.

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Discover your own holiday style. Browse and be inspired.

Top destinations.

Tuscany

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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.

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Meet on Sailsquare, get to know each other on the boat and go home with new friends.

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