Choose your sailing holiday among thousands of unique experiences.
Mary R. 
Giosy D. 
Ausra G. 
Marta A. 
Valentina M. 
Gloriettà C. 
Eric D. 
Giacomo R. 
Eric D. 
Top destinations.
Italy
204 holidays
Tuscany
60 holidays
Liguria
39 holidays
Aeolian Islands
38 holidays
Pontine Islands
9 holidays
Greece
7 holidays
Croatia
4 holidays
Sailsquare is the ultimate connection between skippers and travellers.
Skippers create holidays following their passions, the others will simply enjoy an unforgettable holiday.
Discover who is already on board before you leave!
Meet on Sailsquare, get to know each other on the boat and go home with new friends.
We're here to help before, after or during the holiday
You can contact our customer care or your skipper directly. We're here for you!
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