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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 4511 available holidays!
Discover your own holiday style. Browse and be inspired

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

234 available holidays

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

46 available holidays

Sailing holidays in Malta: discover the ancient heart of the Mediterranean.

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

Top destinations.

Italy

2196 holidays

Greece

638 holidays

Aeolian Islands

423 holidays

Northern Sardinia

364 holidays

Tuscany

351 holidays

Pontine Islands

242 holidays

Croatia

239 holidays

Liguria

175 holidays

Discover all destinations.
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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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