Choose your sailing holiday among thousands of unique experiences.

Destination not found
Find the perfect flotilla for you. Book it. Live it. Discover all ABSOLUTE Flotillas

Discover your own holiday style. Browse and be inspired.

Top destinations.


129 holidays


1034 holidays


148 holidays


347 holidays

Aeolian Islands

161 holidays


137 holidays

Pontine Islands

104 holidays

Balearic Islands

132 holidays

from the blog

5 Greek islands that few people know: discover them on a sailing boat!

  read all

Sailsquare is the ultimate connection between skippers and travelers.

Skippers create holidays following their passions, the others will simply enjoy an unforgettable holiday.

Discover who is already on board before you leave!

Meet on Sailsquare, get to know each other on the boat and go home with new friends.

We're here to help before, after or during the holiday

You can contact our customer care or your skipper directly. We're here for you!

Still uncertain? Give us some details, we'll help you find your perfect holiday! Fill in the form!