Thousands of unique sailing holidays, organised by local skippers.
Pasxalis B. 
Giovanni S. 
Denise C. 
Michele V. 
Veronica S. 
Marica Z. 6 hours ago
Marica Z. 6 hours ago
Marica Z. 6 hours ago
Marina B. 6 hours ago
Christian C. 
Francois P. 
Guido C. 
Mario O. 
Ilario C. 
Top destinations.
Italy
1247 holidays
Greece
494 holidays
Tuscany
279 holidays
Aeolian Islands
234 holidays
Croatia
190 holidays
Pontine Islands
136 holidays
Northern Sardinia
135 holidays
Liguria
106 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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