>

Choose your sailing holiday among thousands of unique experiences.

Destination not found
Discover what holiday style is right for you. Browse through all inspirations.

Top destinations.

Italy

489 holidays

Aeolian

84 holidays

Croatia

84 holidays

Greece

211 holidays

Tuscany

63 holidays

Pontine Islands

41 holidays

Balearic Islands

62 holidays

from the blog

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

  read all

We are the first common ground between skippers and travelers.

Skippers create holidays based on their passions, the others are just busy enjoying their holiday.

Discover who is already on board before leaving!

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

Do you need help, before, after or during the holiday?

You can contact our customer care or directly the skipper who created the holiday. We're here for you!

Still uncertain? Give us some details, we are looking forward to help you finding your perfect holiday! Fill in the form!

Join our community of more than 50.000 registered users!