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
4.5
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
Give this experience a try!
Starting from
€1,200
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
Mauro
has booked
Starting from
€583
Per person
Duration:
6 days - 7 nights
Italy:
Aegadian islands
Give this experience a try!
Starting from
€920
Per person
4.4
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+8 travellers
have booked
Starting from
€1,040
Per person
Duration:
6 days - 7 nights
Italy:
Aegadian islands
Give this experience a try!
€935
Per person
4.0
Duration:
6 days - 7 nights
Italy:
Amalfi Coast
+6 travellers
have booked
Starting from
€1,350
Per person
4.0
Duration:
7 days - 7 nights
Italy:
Pontine Islands
+7 travellers
have booked
Starting from
€800
Per person
3.5
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+4 travellers
have booked
Starting from
€675
€750
Per person
4.5
Duration:
7 days - 7 nights
Italy:
Southern Sardinia
Give this experience a try!
Starting from
€1,691
Per person
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+17 travellers
have booked
€903
€950
Per person
4.6
Duration:
7 days - 6 nights
Italy:
Pontine Islands
Give this experience a try!
Starting from
€855
€900
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Tuscany
+13 travellers
have booked
Starting from
€830
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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