Sailboat yacht sailing holidays & tours in Italy
Discover more than 96 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
96
experiences
96
experiences
5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
6 departures available
September - October
Starting from
€337
Per person
4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
October
€690
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
October - November
€583
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
September
€689
Per person
5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
6 departures available
September - October
Starting from
€337
Per person
4.7
Italy: Tuscany
3 days - 2 nights
3 departures available
October
€200
Per person
4.7
Italy: Sicily
4 days - 3 nights
2 departures available
September
Starting from
€390
€351
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
14 departures available
March - October
Starting from
€200
€180
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
4 departures available
September - October
Starting from
€220
Per person
4.7
Italy: Pantelleria and Lampedusa
6 days - 7 nights
One departure available
September - October
€850
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
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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 - Sailboat yacht sailing holidays & tours in Italy
12542 reviews
Midweek relaxing in the Pontine Islands
09/15/2025
Francesco M.
-
Italy
The Wild Flotilla: dive into the wild nature of Tuscany and Corsica
09/15/2025
Giulia P.
-
Italy
Day trip with aperitif at sunset!
09/15/2025
Michela C.
-
Italy
Pontine Islands aboard a splendid 16-meter sailboat
09/15/2025
Giorgio R.
-
Italy
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