Sailboat yacht sailing holidays & tours in Italy
Discover more than 208 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
208
experiences
208
experiences
5.0
Super!
Italy: Liguria
2 days - 1 night
5 departures available
August - September
€225
Per person
4.9
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€420
Per person
4.8
Super!
Italy: Aeolian Islands
6 days - 6 nights
One departure available
August
€850
Per person
Italy: Southern Sardinia
7 days - 7 nights
3 departures available
August
Starting from
€1,500
€1,350
Per person
4.7
Italy: Liguria
3 days - 3 nights
One departure available
September
€441
Per person
4.4
Italy: Aeolian Islands
6 days - 7 nights
2 departures available
August - September
Starting from
€940
Per person
5.0
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
August - October
Starting from
€540
Per person
5.0
Italy: Tuscany
6 days - 6 nights
2 departures available
August - October
Starting from
€559
Per person
Italy: Pontine Islands
3 days - 3 nights
One departure available
August
€400
Per person
5.0
Italy: Pontine Islands
3 days - 2 nights
6 departures available
September - October
Starting from
€337
Per person
4.6
Italy: Tuscany
7 days - 7 nights
2 departures available
August - September
€650
Per person
4.9
Italy: Sicily
9 days - 10 nights
One departure available
August
€1,300
Per person
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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 - Sailboat yacht sailing holidays & tours in Italy
11729 reviews
Four-day cruise to Elba or Capraia - Hostess on board
08/1/2025
Veronica M.
-
Italy
Midweek relaxing in the Pontine Mountains
08/1/2025
Valentina P.
North Corsica & Tuscan Archipelago: we love to travel a lot
08/1/2025
Sandro G.
-
Italy
Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms
08/1/2025
Michele A.
-
Netherlands
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