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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 4439 available holidays!
Discover your own holiday style. Browse and be inspired

Sailing holidays in Greece: discover the thousands islands of the Greek Archipelago.

636 available holidays

All-inclusive sailing holidays: just sit back, relax, and enjoy life onboard.

234 available holidays

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

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

Top destinations.

Italy

2177 holidays

Greece

636 holidays

Aeolian Islands

412 holidays

Northern Sardinia

365 holidays

Tuscany

351 holidays

Pontine Islands

240 holidays

Croatia

237 holidays

Liguria

173 holidays

Discover all destinations.
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Sailing in Antarctica: a story to the end of the world

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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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