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
5 departures available
August - September
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
13641 reviews
Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation
09/17/2025
Mauro Z.
-
Italy
Weekend at the Pontine aboard a splendid 16-meter sailboat
09/17/2025
Giulia E.
-
Italy
Egadi paradise for sailing and snorkeling
09/17/2025
Vicky H.
-
Belgium
A week in the Aeolian Islands - 6 islands in seven days
09/17/2025
Giuseppe I.
-
Italy
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