Yacht sailing holidays & skippered tours in Italy
Discover more than 2 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
2
experiences
2
experiences
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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.
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
12522 reviews
Short sailing cruise in the Gulf of Naples
07/11/2025
Daniela D.
-
Italy
Life-changing experiences - Escape to the Pontine Islands
07/11/2025
Emanuela P.
Sailing weekend in the Pontine Islands
07/10/2025
Stefano M.
-
Italy
Dream sailing on a fully-equipped catamaran
07/9/2025
Alessandro B.
-
Italy
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