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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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
13628 reviews
Scopello, San Vito and Egadi: friends, good food sailing
09/17/2025
Maurizio M.
-
Italy
Midweek relaxing in the Pontine Islands
09/17/2025
Giovanna M.
-
Italy
Long weekend of whale watching with WWF guide on an 18-meter schooner
09/16/2025
Paolo S.
-
Italy
Capri LightBlue and Positano BluSKy
09/16/2025
Claudia D.
-
Italy
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