Thousands of unique sailing holidays, organised by local skippers.

Travel alone or in a group, and meet new sailing friends.
from the blog

10 hidden travel treasures, only accessible by boat

  read all

Sailsquare offers an ultimate connection between skippers and travellers.

Skippers create holidays following their passion, travellers will be able to simply enjoy an unforgettable holiday.

Discover who is already on board before you set sail!

Introduce yourself on Sailsquare, get to know each other on board, go home with new friends.

We're here to help you before, during and after your holiday.

You can contact our customer care team, or contact your skipper directly. We're all here to help offer support and guidance!

Discover Sailsquare

Try our holiday concierge service!

Can't find exactly what you're looking for? Try our free concierge service​! Let us help you find the experience that's just right for you.

Use holiday concierge

Need some help?

Would you like some support using the platform or when making an online payment? We've (almost) always got the answers!
Contact us