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

309 holidays

Greece

97 holidays

Aeolian Islands

94 holidays

Tuscany

57 holidays

Liguria

23 holidays

Pontine Islands

18 holidays

Croatia

16 holidays

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A sailing holiday is good for you: 5 scientific reasons to prove it.

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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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You have clear ideas about your perfect holiday but it's not among the available listings? Get in touch with us, we will find a solution together!

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