Choose your holiday from thousands of unique sailing experiences.

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Discover your own holiday style. Browse and be inspired.

Top destinations.

Italy

749 holidays

Greece

268 holidays

Tuscany

163 holidays

Croatia

144 holidays

Aeolian Islands

142 holidays

Pontine Islands

62 holidays

Liguria

60 holidays

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5 Greek islands that few people know: discover them on a sailing boat!

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Sailsquare offers an ultimate connection between skippers and travellers.

Skippers create holidays following their passion, travellers will be able to simply enjoy an unforgettable holiday.

Discover who is already on board before you set sail!

Introduce yourself on Sailsquare, get to know each other on board, go home with new friends.

We're here to help you before, during and after your holiday.

You can contact our customer care team, or contact your skipper directly. We're all here to help offer support and guidance!

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