Choose your sailing holiday among thousands of unique experiences.
Matteo M. 10 minutes ago
Lorenzo F. 12 minutes ago
Lorenzo F. 23 minutes ago
Alberto U. 45 minutes ago
Federico C. 47 minutes ago
Michela F. 57 minutes ago
Francesco Paolo S. 
Angelo V. 
Mauro T. 2 hours ago
Enrico A. 2 hours ago
Cesare B. 2 hours ago
Antonella P. 2 hours ago
Emanuele R. 2 hours ago
Gabriele M. 3 hours ago
Elena D. 
Rodolphe C. Top destinations.
Italy
529 holidays
Greece
118 holidays
Tuscany
99 holidays
Aeolian Islands
91 holidays
Pontine Islands
82 holidays
Liguria
50 holidays
Croatia
7 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!