Yacht sailing holidays & skippered tours in Italy
Discover more than 142 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
142
experiences
142
experiences
5.0
Duration:
2 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
€275
Per person
4.7
Duration:
2 days - 2 nights
Italy:
Gulf of Naples
Give this experience a try!
Starting from
€260
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
€250
Per person
4.8
Duration:
2 days - 2 nights
Italy:
Tuscany
+22 travellers
have booked
€212
Per person
4.5
Duration:
2 days - 2 nights
Italy:
Amalfi Coast
+21 travellers
have booked
Starting from
€252
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Liguria
+8 travellers
have booked
Starting from
€201
Per person
4.8
Duration:
2 days - 2 nights
Italy:
Tuscany
+15 travellers
have booked
€260
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
+7 travellers
have booked
€200
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€300
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Liguria
+23 travellers
have booked
€261
€275
Per person
4.9
Duration:
2 days - 2 nights
Italy:
Tuscany
+4 travellers
have booked
Starting from
€220
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
+2 travellers
have booked
Starting from
€290
Per person
Why book a holiday with Sailsquare?
The world's largest marketplace for sailing holidays
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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