Yacht sailing holidays & skippered tours in Italy
Discover more than 258 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
258
experiences
258
experiences
5.0
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
+3 travellers
have booked
€1,400
Per person
5.0
Duration:
3 days - 3 nights
Italy:
Southern Sardinia
Give this experience a try!
€780
Per person
4.3
Duration:
4 days - 5 nights
Italy:
Tuscany
Give this experience a try!
€429
Per person
4.8
Duration:
4 days - 4 nights
Italy:
Tuscany
Give this experience a try!
€497
€552
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Liguria
+7 travellers
have booked
€342
€380
Per person
5.0
Duration:
6 days - 6 nights
Italy:
Aeolian Islands
+55 travellers
have booked
Starting from
€998
Per person
Duration:
3 days - 2 nights
Italy:
Sicily
Give this experience a try!
€801
€890
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Lake Garda
+10 travellers
have booked
Starting from
€85
Per person
5.0
Duration:
4 days - 3 nights
Italy:
Pontine Islands
+5 travellers
have booked
€460
Per person
5.0
Duration:
5 days - 4 nights
Italy:
Tuscany
+2 travellers
have booked
€550
Per person
4.9
Duration:
3 days - 3 nights
Italy:
Pontine Islands
+23 travellers
have booked
Starting from
€371
€390
Per person
4.8
Duration:
1 day - 0 nights
Italy:
Liguria
+3 travellers
have booked
€50
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
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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 - Yacht sailing holidays & skippered tours in Italy
10929 reviews
Let's discover the Aeolian Islands together by sailing
05/18/2024
Eros Giorgio M.
-
Italy
Weekend at the Pontine Islands: Ponza and Palmarola
05/18/2024
Giulio S.
-
Italy
In the blue of Capri and the infinity of the Amalfi Coast
05/15/2024
simona b.
An unforgettable sail to discover the Egadi Islands
05/14/2024
Marco B.
-
Switzerland
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