Thousands of unique sailing holidays, organised by local skippers.
Tommaso F. 34 minutes ago
Rita G. 37 minutes ago
Rita G. 38 minutes ago
Jen W. 2 hours ago
Jen W. 4 hours ago
ALESSANDRA D. 5 hours ago
Vincenzo O. 
Marta M. 
Gianpietro C. 5 hours ago
Elena S. 5 hours ago
Alessandro B. 5 hours ago
Enrica V. 5 hours ago
GIUSEPPE C. 5 hours ago
Luca C. 5 hours ago
Dominikus L. 
Stefania R. 6 hours ago
Matteo C. 6 hours ago
Cinzia T. 
Edoardo B. 
Top destinations.
Italy
2052 holidays
Greece
552 holidays
Aeolian Islands
393 holidays
Northern Sardinia
391 holidays
Tuscany
335 holidays
Croatia
244 holidays
Pontine Islands
232 holidays
Liguria
148 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!