You can choose among 413 unique sailing holidays proposals.

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Unique holidays, at a fair price

Every holiday on sailsquare has the personality of whom creates it: that's why every experience is unique. Moreover, since these 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. They are real people who want to live, share and pass on to others their passion.

Join as skipper

If you are not satisfied neither are we

We strive to make our service better and more efficient every day and to deliver you unforgettable experiences. However, should anything go wrong for some reason, you can still change your mind..

Our cancellation policy

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