You can choose among 1217 unique sailing experiences.

Invite a friend and earn credits for your sailing holidays!

Amazing holidays at a fair price

Each holiday takes after who creates and shapes it: that’s why each experience is one of a kind. Besides, as the holidays are created by private users, they are cheaper than those listed by traditional tour operators.

Find your next holiday

We don’t have “plain” skippers

On sailsquare, skippers are not just sea “drivers”, but expert sailors, mainly motivated by their love for sailing and the sea, real people craving to share and instill their passion to others.

Apply as a skipper

Lost in the sea? We are here to help you out.

We are working hard everyday to make our service better and more efficient in order to guarantee unforgettable experiences. Our customer care is skilled and ready to help you by answering to any possible question.

Contact our Customer Care

Do you own a boat? Earn money and decrease the running costs while sailing!