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

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

178 available holidays

Discover real nature on a sailboat.

387 available holidays

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

112 available holidays

Discover your own holiday style. Browse and be inspired.

Top destinations.

Tuscany

149 holidays

Italy

1116 holidays

Aeolian Islands

214 holidays

Pontine Islands

72 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

202 holidays

Liguria

111 holidays

Croatia

130 holidays

Greece

405 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 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.

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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