
Yacht sailing holidays & skippered tours in Italy
Discover more than 1 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
1
experience
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Get onboard solo, with your family or your friends
Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.
Find out before you book who's waiting for you on board
Find out more about the skipper and travellers who have already booked the holiday, to find out more about the
Sailing holidays that suit all budgets
On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.
Reviews - Yacht sailing holidays & skippered tours in Italy
13868 reviews
A bridge in the blue - June 2 on a sailing boat
06/9/2026
Sara M.
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IT
Weekend of the Pontine Islands to discover Ponza and Palmarola
06/9/2026
Giacomo G.
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CH
Weekend at the Pontine Islands
06/9/2026
Marco N.
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IT
June 2nd long weekend between Procida, Ischia and Ventotene
06/9/2026
Biagio G.
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IT
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