Daniele T. 
Michele P. 
Sailor5537 
Benedetta P. 
Nicola C. 
Agnese M. 
Mario I. 
Sailor5440 S. 
Flavia F. 
Lara P. 
Sailing
Choose your sailing holidays among hundreds all over the world
Meet new people like you
Live unique experiences and get back to the ground with new friends
Upcoming holidays
Sailing
Montecristo Island from Punta Ala
from
380€
to 430€
to 430€
per person
from 26 April to 3 May
Tuscany• Italy
Tuscany• Italy
Only invited people admitted
You can choose among 147 unique sailing holidays proposals.
Unique holidays, at a fair price
Every holiday on sailsquare looks like who creates and gives life to it: that's why every experience is unique. Moreover, since that holidays are organized by private users, they are cheaper than those offered by traditional tour operators.
Find your next holidayOurs are not “simply” skippers
On sailsquare, skippers are not "drivers" of the sea, but experienced sailors, first of all motivated by their love for the sea and sailing, real people who want to share and pass on to others their passion.
Become a sailsquare skipperIf you are not satisfied neither are we
We strive every day to make our service better and more efficient and to guarantee you unforgettable experiences. But if, for some reason, something should go wrong...
Our cancellation policy