Choose your sailing holiday among thousands of unique experiences.

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Top destinations.

Italy

280 holidays

Greece

95 holidays

Aeolian Islands

89 holidays

Tuscany

54 holidays

Liguria

23 holidays

Pontine Islands

18 holidays

Croatia

13 holidays

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A sailing holiday is good for you: 5 scientific reasons to prove it.

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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.

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Meet on Sailsquare, get to know each other on the boat and go home with new friends.

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