Thousands of unique sailing holidays, organised by local skippers.
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Irene P. 12 minutes ago
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Biagio F. 22 minutes ago
Walter P. 28 minutes ago
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Khadine A. 
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Recep M. 
Top destinations.
Italy
1710 holidays
Greece
625 holidays
Tuscany
341 holidays
Aeolian Islands
284 holidays
Croatia
230 holidays
Northern Sardinia
192 holidays
Pontine Islands
190 holidays
Liguria
131 holidays
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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