Choose from thousands of unique sailing holidays, organised by local skippers.
Antun R. 
Andrea M. 
Marco Attilio G. 
Maurizio C. 
Céline L. 
Claudia S. 
Pierre L. 
Patrick P. 
Flavio C. 
Manuele S. 
Nikos P. 
Top destinations.
Italy
755 holidays
Greece
301 holidays
Tuscany
165 holidays
Croatia
155 holidays
Aeolian Islands
142 holidays
Pontine Islands
62 holidays
Liguria
60 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!