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Choose your sailing holiday among thousands of unique experiences.

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Travel alone or in a group and meet new sailing friends.
Discover your own holiday style. Browse and be inspired.

Wishing for a sailing holiday with your family? Time to make your dream come true.

20 available holidays

Sailing holidays for fun addicted!

21 available holidays

All-Inclusive sailing holidays: just relax and enjoy life onboard.

47 available holidays

Top destinations.

Italy

529 holidays

Greece

118 holidays

Tuscany

99 holidays

Aeolian Islands

91 holidays

Pontine Islands

82 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

66 holidays

Liguria

50 holidays

Croatia

7 holidays

Discover all destinations.
from the blog

Questions, doubts and interesting facts for sailing boat beginners

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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!

Discover Sailsquare

Still need to find the right holiday?

You have clear ideas about your perfect holiday but it's not among the available listings? Get in touch with us, we will find a solution together!

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