Thousands of unique sailing holidays, organised by local skippers.
Travel alone or in a group, and meet new sailing friends.
Domenico C. 
David K. 
Pierre G. 
Dario . 
Livio M. 
Jean Luc M. 
Ausra G. 
Julia B. 
Andrea D. Our favourites.
Catamaran sailing holidays with a skipper
Sailing holidays in the Balearic Islands with a local skipper
Sailing holidays in Croatia with a local skipper
Hire a whole boat with skipper
Venice and the Gulf of Trieste
Sailing holidays in Split with a local skipper
Sailing holidays in Greece with a local skipper
Sailing courses & regatta with professional skipper
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!
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Can't find exactly what you're looking for? Try our free concierge service! Let us help you find the experience that's just right for you.
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