
Sailboat yacht sailing holidays & tours in Italy
Discover more than 53 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
53
experiences

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

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
14 departures available
June - September
Starting from
€625
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
24 departures available
May - October
Starting from
€600
Per person

4.6
Italy: Northern Sardinia
6 days - 7 nights
19 departures available
May - October
Starting from
€600
€540
Per person

4.9
Super!
Italy: Liguria
2 days - 2 nights
One departure available
May
€360
Per person

4.9
Super!
Italy: Liguria
2 days - 2 nights
One departure available
June
€360
Per person

4.9
Super!
Italy: Tuscany
4 days - 3 nights
16 departures available
May - September
Starting from
€430
€409
Per person

5.0
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
October - November
€350
Per person

5.0
Super!
Italy: Lake Garda
2 days - 2 nights
One departure available
May
€189
Per person

5.0
Super!
Italy: Lake Garda
1 day - 0 nights
One departure available
June
€69
Per person

5.0
Super!
Italy: Lake Garda
1 day - 0 nights
One departure available
May
€59
Per person

4.8
Super!
Italy: Pontine Islands
4 days - 3 nights
17 departures available
April - July
Starting from
€210
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
12660 reviews
North-East Sardinia and South Corsica on a sailing boat with gourmet cuisine
10/25/2025
Teresa B.
-
Germany
Barcolana weekend in Trieste and surroundings.
10/24/2025
Marilisa V.
-
Italy
Weekend in Capraia, the island with timeless sunsets
10/22/2025
Don D.
-
Italy
Relaxing weekend between Portovenere and the 5 Terre
10/21/2025
Manuela S.
-
Italy
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