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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 4515 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.

41 available holidays

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

258 available holidays

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

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

Top destinations.

Italy

2090 holidays

Greece

667 holidays

Tuscany

375 holidays

Aeolian Islands

357 holidays

Northern Sardinia

321 holidays

Croatia

258 holidays

Pontine Islands

232 holidays

Liguria

152 holidays

Discover all destinations.
from the blog

Renato and Luciana: how a sailing experience can change your life forever

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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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