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
4.8
Super!
Italy: Tuscany
2 days - 2 nights
5 departures available
July - August
Starting from
€200
€180
Per person
4.6
Premium
Italy: Northern Sardinia
7 days - 7 nights
4 departures available
July - August
Starting from
€1,455
€1,382
Per person
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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.
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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
13644 reviews
Summer is made for the Aeolian Islands! Weekly cruise
09/18/2025
Jurij P.
-
Italy
Midweek special on the island of Elba, 2 nights
09/18/2025
Roberta Anna P.
-
Italy
Relaxing weekend between Portovenere and the 5 Terre
09/18/2025
Silvia I.
-
Italy
Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation
09/17/2025
Mauro Z.
-
Italy
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