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Thousands of unique sailing holidays, organised by local skippers.

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Travel alone or in a group, and meet new sailing friends.
Discover the other 3433 available holidays!
Discover your own holiday style. Browse and be inspired

The Balearic Islands

239 available holidays

Dreaming about family sailing holidays? It's time to make that dream a reality.

39 available holidays

Sailing holidays in Croatia: discover the islands, islets, and reefs of the Croatian Archipelago.

191 available holidays
Flotillas on a sailing boat: the best 50 experiences. See all Flotillas experiences.

Top destinations.

Italy

1599 holidays

Greece

405 holidays

Northern Sardinia

341 holidays

Aeolian Islands

272 holidays

Tuscany

249 holidays

Croatia

191 holidays

Pontine Islands

170 holidays

Liguria

96 holidays

Discover all destinations.
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10 hidden travel treasures, only accessible by 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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Still looking for the right holiday ?

You have some idea of your perfect holiday, but can't find what you're looking for? Get in touch! We can find the right experience together!

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