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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 the other 2806 holidays currently available!
Discover your own holiday style. Browse and be inspired.

Sailing holidays for fun addicted!

87 available holidays

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

113 available holidays

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

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

Top destinations.

Italy

1354 holidays

Greece

369 holidays

Aeolian Islands

283 holidays

Tuscany

265 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

243 holidays

Croatia

141 holidays

Pontine Islands

103 holidays

Liguria

79 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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