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

189 available holidays

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

137 available holidays

Discover real nature on a sailboat.

434 available holidays

Discover your own holiday style. Browse and be inspired.

Top destinations.

Italy

746 holidays

Tuscany

112 holidays

Aeolian Islands

140 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

144 holidays

Croatia

95 holidays

Pontine Islands

46 holidays

Greece

262 holidays

Liguria

80 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 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.

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

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