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Choose your sailing holiday among thousands of unique experiences.

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Discover your own holiday style. Browse and be inspired.

Top destinations.

Italy

695 holidays

Greece

212 holidays

Aeolian Islands

87 holidays

Tuscany

80 holidays

Liguria

145 holidays

Balearic Islands

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Croatia

58 holidays

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.

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

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