Yacht sailing holidays & skippered tours in Italy
Discover more than 138 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
138
experiences
138
experiences
5.0
Duration:
1 day - 0 nights
Italy:
Lake Garda
+27 travellers
have booked
€99
Per person
4.4
Duration:
1 day - 0 nights
Italy:
Northern Sardinia
Give this experience a try!
€90
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Lake Garda
+48 travellers
have booked
Starting from
€99
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Tuscany
Give this experience a try!
€130
Per person
4.6
Duration:
5 days - 5 nights
Italy:
Tuscany
+3 travellers
have booked
€480
Per person
5.0
Duration:
3 days - 3 nights
Italy:
Tuscany
Give this experience a try!
€361
€380
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
+18 travellers
have booked
€225
Per person
5.0
Duration:
3 days - 3 nights
Italy:
Pontine Islands
Give this experience a try!
€360
Per person
4.3
Duration:
3 days - 3 nights
Italy:
Tuscany
Give this experience a try!
€399
Per person
4.9
Duration:
3 days - 3 nights
Italy:
Aeolian Islands
Give this experience a try!
€265
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
Starting from
€356
€375
Per person
4.8
Duration:
3 days - 3 nights
Italy:
Tuscany
+2 travellers
have booked
Starting from
€324
€360
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 - Yacht sailing holidays & skippered tours in Italy
10913 reviews
Weekend in Capraia, the island with timeless sunsets
05/7/2024
Irene T.
-
Italy
Week End Basic and Advanced Sailing Course
05/7/2024
Federico B.
-
Italy
1st May - Whale watching cruise with WWF researcher between Elba and Capraia
05/6/2024
Elettra B.
-
Italy
Catamaran weekend: La Spezia, Portovevere, Lerici and Cinque Terre
05/6/2024
Paola d.
-
Italy
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