Yacht sailing holidays & skippered tours in Italy
Discover more than 237 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
237
experiences
237
experiences
4.5
Duration:
2 days - 2 nights
Italy:
Amalfi Coast
+21 travellers
have booked
€294
€309
Per person
4.8
Duration:
2 days - 2 nights
Italy:
Tuscany
+15 travellers
have booked
€349
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
+7 travellers
have booked
€250
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Liguria
+23 travellers
have booked
Starting from
€285
€300
Per person
4.2
Duration:
2 days - 2 nights
Italy:
Liguria
+5 travellers
have booked
€290
Per person
4.7
Duration:
2 days - 2 nights
Italy:
Gulf of Naples
Give this experience a try!
Starting from
€250
Per person
4.5
Duration:
7 days - 7 nights
Italy:
Tuscany
Give this experience a try!
€980
Per person
4.8
Duration:
2 days - 2 nights
Italy:
Venice and the Gulf of Trieste
Give this experience a try!
€290
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€315
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Lake Garda
+50 travellers
have booked
Starting from
€119
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Liguria
+12 travellers
have booked
€128
€142
Per person
5.0
Duration:
8 days - 7 nights
Italy:
Sicily
Give this experience a try!
€650
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
10917 reviews
25 April - Whale watching expedition with WWF researcher in Liguria
05/8/2024
Nicoletta S.
-
Italy
Weekend with wine tasting between Santa Margherita Ligure and Portofino
05/7/2024
Valentina B.
-
Italy
Week End Basic and Advanced Sailing Course
05/7/2024
Antonio R.
-
Italy
Weekend in Capraia, the island with timeless sunsets
05/7/2024
enrico g.
-
Italy
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