Thousands of unique sailing holidays, organised by local skippers.
Marié Claire G. 18 minutes ago
Francesca M. 46 minutes ago
Daisy L. 
Melania G. 7 hours ago
Federica B. 8 hours ago
Federica B. 8 hours ago
Dora B. 9 hours ago
Helen A. 
Serena B. 
Chiara G. 10 hours ago
Arianna G. 10 hours ago
Guido A. 10 hours ago
Marco C. 11 hours ago
Barbara A.
Andrés F. 11 hours ago
Andrés F. 11 hours ago
Katrina V. 
Roberta M. 
Top destinations.
Italy
2102 holidays
Greece
644 holidays
Aeolian Islands
396 holidays
Northern Sardinia
342 holidays
Tuscany
341 holidays
Pontine Islands
238 holidays
Croatia
236 holidays
Liguria
162 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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Would like some support using the platform or making an online payment? We've (almost) always got the answers!