Yacht sailing holidays & skippered tours in Italy
Discover more than 83 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
83
experiences
83
experiences
5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
One departure available
September
Starting from
€337
Per person
5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
3 departures available
September - October
Starting from
€337
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
September - October
€950
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
September
€689
Per person
4.7
Italy: Tuscany
3 days - 3 nights
One departure available
September
€441
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
2 departures available
September
Starting from
€220
Per person
4.9
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
September
Starting from
€200
€180
Per person
4.7
Italy: Pantelleria and Lampedusa
6 days - 7 nights
One departure available
September - October
€850
Per person
4.7
Italy: Sicily
4 days - 3 nights
2 departures available
September
Starting from
€390
€351
Per person
4.9
Super!
Italy: Liguria
2 days - 1 night
2 departures available
September
€260
Per person
4.8
Super!
Italy: Liguria
2 days - 1 night
One departure available
September
€260
Per person
4.8
Super!
Italy: Liguria
1 day - 0 nights
One departure available
September
€65
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
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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
13591 reviews
Midweek relaxing in the Pontine Islands
09/13/2025
Alessandra S.
-
Italy
The Egadi Islands as you've never seen them on a 16-meter boat
09/13/2025
Rosario P.
-
Italy
4 days in the Pontine Islands (sailing school)
09/13/2025
Erica M.
-
Italy
4 days in the Pontine Islands (sailing school)
09/13/2025
Chiara C.
-
Italy
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