Choose your sailing holiday among thousands of unique experiences.
Michael G. 
Isabella C. 6 hours ago
Lorenzo Q. 8 hours ago
Francesca F. 
Francesca C.
Daniele R. 11 hours ago
Fabio Z. 16 hours ago
Fabio Z. 16 hours ago
Margarita A. 17 hours ago
Simona N. 23 hours ago
Simona N. 23 hours ago
Fabio O. 
Luca F. 
Emanuela L. 
Alessandro B. 
Enrico Maria F. 
Francesco G. 
Nicla R. 
Francesca N. 
Giulia B. 
Top destinations.
Italy
190 holidays
Aeolian Islands
66 holidays
Tuscany
28 holidays
Liguria
15 holidays
Greece
14 holidays
Croatia
6 holidays
Pontine Islands
5 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!
Still need to find the right holiday?
You have clear ideas about your perfect holiday but it's not among the available listings? Get in touch with us, we will find a solution together!
Need help?
You need support to use the platform or to make a payment online? You need info or there is something that doesn't add up? For - almost - any question we have an answer!