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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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Sailing holidays for fun addicted!

90 available holidays

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

61 available holidays

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

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

Top destinations.

Italy

1123 holidays

Greece

311 holidays

Tuscany

230 holidays

Aeolian Islands

215 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

196 holidays

Croatia

123 holidays

Pontine Islands

119 holidays

Liguria

74 holidays

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from the blog

5 Greek islands that few people know: discover them on a sailing boat!

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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.

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You can contact our customer care or your skipper directly. We're here for you!

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