Toggle menu
contact us
>

Choose your sailing holiday among thousands of unique experiences.

Destination not found
Travel alone or in a group and meet new sailing friends.

Our favorites.

Discover the other 2683 holidays currently available!
Find the perfect flotilla for you. Book it. Live it. Discover all ABSOLUTE Flotillas

Spring weekend on a sailing boat: discover unexpected treasures.

32 available holidays

Wishing for a sailing holiday with your family? Time to make your dream come true.

83 available holidays

All-Inclusive sailing holidays: just relax and enjoy life onboard.

201 available holidays

Discover your own holiday style. Browse and be inspired.

Top destinations.

Tuscany

167 holidays

Aeolian Islands

200 holidays

Italy

1149 holidays

Pontine Islands

97 holidays

Liguria

120 holidays

Greece

400 holidays

Balearic Islands

132 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

211 holidays

Discover all destinations.
from the blog

A sailing holiday is good for you: 5 scientific reasons to prove it.

  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!

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

Join our community of more than 50.000 travellers!

Sign up now