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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.
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Discover your own holiday style. Browse and be inspired

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

411 available holidays

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

163 available holidays

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

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

Top destinations.

Italy

1628 holidays

Greece

410 holidays

Northern Sardinia

339 holidays

Aeolian Islands

272 holidays

Tuscany

256 holidays

Croatia

187 holidays

Pontine Islands

180 holidays

Liguria

104 holidays

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from the blog

ALOTS: Episode 7 – The Caribbean of Europe: A Sardinian sailing adventure

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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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