Yacht sailing holidays & skippered tours in Italy
Discover more than 200 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
200
experiences
200
experiences
Duration:
2 days - 2 nights
Italy:
Liguria
+44 travellers
have booked
€240
Per person
4.5
Duration:
7 days - 7 nights
Italy:
Tuscany
Give this experience a try!
€980
Per person
5.0
Duration:
6 days - 6 nights
Italy:
Tuscany
+9 travellers
have booked
Starting from
€650
Per person
5.0
Duration:
6 days - 5 nights
Italy:
Pontine Islands
Give this experience a try!
€720
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Liguria
+12 travellers
have booked
€130
€144
Per person
4.5
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
Give this experience a try!
Starting from
€800
Per person
4.8
Duration:
2 days - 1 night
Italy:
Liguria
+2 travellers
have booked
Starting from
€270
Per person
4.5
Duration:
8 days - 7 nights
Italy:
Aeolian Islands
Give this experience a try!
€850
Per person
5.0
Duration:
7 days - 6 nights
Italy:
Tuscany
+8 travellers
have booked
€780
Per person
4.9
Duration:
1 day - 0 nights
Italy:
Liguria
+153 travellers
have booked
€149
Per person
4.9
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
+37 travellers
have booked
Starting from
€713
€750
Per person
5.0
Duration:
6 days - 6 nights
Italy:
Tuscany
+3 travellers
have booked
Starting from
€756
€840
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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