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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 4092 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.

38 available holidays

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

552 available holidays

The Balearic Islands

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

Top destinations.

Italy

2005 holidays

Greece

552 holidays

Aeolian Islands

395 holidays

Northern Sardinia

386 holidays

Tuscany

315 holidays

Croatia

240 holidays

Pontine Islands

215 holidays

Liguria

147 holidays

Discover all destinations.
from the blog

Cheap sailing holidays: Mediterranean and Greece

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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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