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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.

Greece

152 holidays

Caribbean

46 holidays

Italy

515 holidays

Aeolian islands

56 holidays

Liguria

150 holidays

Tuscany

45 holidays

Balearic Islands

18 holidays

from the blog

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

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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!