
Sailboat yacht sailing holidays & tours in Italy
Discover more than 345 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
345
experiences

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
11 departures available
June - September
Starting from
€750
€675
Per person

4.8
Italy: Northern Sardinia
6 days - 7 nights
14 departures available
June - October
Starting from
€590
Per person

4.6
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
August
Starting from
€1,260
€1,134
Per person

4.7
Italy: Naples & Amalfi Coast
3 days - 3 nights
One departure available
July
€390
€351
Per person

4.7
Italy: Pontine Islands
7 days - 7 nights
4 departures available
July - September
Starting from
€795
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
10 departures available
June - September
Starting from
€620
€558
Per person

4.6
Italy: Pontine Islands
4 days - 3 nights
One departure available
July
€490
Per person

4.7
Italy: Tuscany
6 days - 6 nights
One departure available
July
Starting from
€1,052
Per person

5.0
Super!
Italy: Tuscany
6 days - 7 nights
4 departures available
June - September
Starting from
€950
€855
Per person

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

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
One departure available
July
€350
Per person
4.6
Italy: Tuscany
2 days - 2 nights
35 departures available
January - December
Starting from
€300
€270
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.
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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
12826 reviews
Weekend between Ponza and Palmarola Comfortable - max 4 people
06/18/2026
Cecilia M.
-
IT
Weekend of sea and colors between Ischia, Procida and Vivara
06/17/2026
Domenico T.
Weekend of sea and colors between Ischia, Procida and Vivara
06/17/2026
Domenico R.
Weekend of sea and colors between Ischia, Procida and Vivara
06/17/2026
Sabrina C.
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