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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

You can choose among 149 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 holiday

Ours 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 skipper

If 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

Are you a boat owner? Bring down the running costs of your boat!

Discover our boat owner program