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Choose from 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 2181 available holidays!
Discover your own holiday style. Browse and be inspired

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

29 available holidays

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

164 available holidays

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

245 available holidays

Top destinations.

Italy

836 holidays

Greece

323 holidays

Tuscany

181 holidays

Croatia

164 holidays

Aeolian Islands

143 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

120 holidays

Pontine Islands

74 holidays

Liguria

69 holidays

Discover all destinations.
from the blog

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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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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