>

Choose your sailing holiday among thousands of unique experiences.

Destination not found
Not just sailing: adventure travel and more, for all tastes. Browse all experiences

Discover your own holiday style. Browse and be inspired.

Top destinations.

Caribbean

188 holidays

Italy

136 holidays

Tuscany

56 holidays

Liguria

21 holidays

Canary Islands

65 holidays

Guadeloupe

42 holidays

France

56 holidays

French Riviera

24 holidays

from the blog

Sailing holidays: embrace a peaceful state of mind

  read all

Sailsquare is the ultimate connection between skippers and travellers.

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!

Need help?

You need support to use the platform or to make a payment online? You need info or there is something that doesn't add up? For - almost - any question we have an answer!

Go to the help centre!