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Choose your sailing holiday among thousands of unique experiences.

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Discover your own holiday style. Browse and be inspired.

Top destinations.

Italy

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Greece

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from the blog

Sailing holidays: embrace a peaceful state of mind

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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!

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