
Sailboat yacht sailing holidays & tours in Italy
Discover more than 362 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
362
experiences

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
17 departures available
May - October
Starting from
€689
Per person

4.6
Italy: Northern Sardinia
6 days - 7 nights
16 departures available
May - October
Starting from
€650
€585
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
20 departures available
May - October
Starting from
€590
Per person

4.9
Italy: Aeolian Islands
7 days - 7 nights
22 departures available
May - November
Starting from
€600
€540
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
21 departures available
May - October
Starting from
€640
€576
Per person

4.6
Italy: Pontine Islands
3 days - 2 nights
7 departures available
May - June
Starting from
€230
€207
Per person

5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
9 departures available
April - July
Starting from
€360
Per person

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
5 departures available
May - July
Starting from
€350
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
14 departures available
June - September
Starting from
€680
Per person

4.8
Super!
Italy: Southern Sardinia
6 days - 7 nights
One departure available
May
€550
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
8 departures available
July - September
€1,600
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
12 departures available
June - September
Starting from
€550
€523
Per person
Why book a holiday with Sailsquare?
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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
12670 reviews
Easter on the Island of Elba
04/9/2026
Miriam C.
-
Italy
Easter in Capraia and Corsica
04/9/2026
Monica L.
-
Italy
Easter: Whale Watching Expedition in Pelagos Sanctuary with WWF Guide
04/8/2026
Agnese F.
-
Italy
Easter in Capraia and Corsica
04/8/2026
Giovanni G.
-
Italy
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