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Choose your sailing holiday among thousands of unique experiences.

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Discover your own holiday style. Browse through all inspirations.

Top destinations.

Italy

168 holidays

Aeolian

11 holidays

Croatia

14 holidays

Tuscany

29 holidays

Greece

63 holidays

Pontine Islands

14 holidays

Egadi Islands

16 holidays

from the blog

Questions, doubts and interesting facts for sailing boat beginners

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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!