Thousands of unique sailing holidays, organised by local skippers.

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Top destinations.

Italy

1327 holidays

Greece

509 holidays

Tuscany

287 holidays

Aeolian Islands

237 holidays

Croatia

193 holidays

Pontine Islands

151 holidays

Northern Sardinia

139 holidays

Liguria

107 holidays

from the blog

Sailing holidays: embrace a peaceful state of mind

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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!

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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