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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.
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Discover your own holiday style. Browse and be inspired.

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

134 available holidays

Sailing holidays for fun addicted!

64 available holidays

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

135 available holidays
Find the perfect flotilla for you. Book it. Live it. Discover all ABSOLUTE Flotillas

Top destinations.

Italy

1338 holidays

Greece

497 holidays

Corsica

271 holidays

Aeolian Islands

234 holidays

Tuscany

289 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

191 holidays

Liguria

118 holidays

Balearic Islands

223 holidays

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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!

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