Yacht sailing holidays & skippered tours in Italy
Discover more than 130 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
130
experiences
130
experiences
4.5
Duration:
2 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€370
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Liguria
+23 travellers
have booked
€280
€295
Per person
4.7
Duration:
2 days - 2 nights
Italy:
Gulf of Naples
Give this experience a try!
Starting from
€250
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+2 travellers
have booked
€727
€765
Per person
Duration:
2 days - 2 nights
Italy:
Liguria
+44 travellers
have booked
€190
Per person
4.8
Duration:
2 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€216
€240
Per person
4.8
Duration:
2 days - 1 night
Italy:
Liguria
+2 travellers
have booked
€270
Per person
5.0
Duration:
7 days - 7 nights
Italy:
Tuscany
+2 travellers
have booked
€850
Per person
4.9
Duration:
7 days - 6 nights
Italy:
Tuscany
Give this experience a try!
€500
Per person
4.9
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
+36 travellers
have booked
Starting from
€646
€680
Per person
5.0
Duration:
6 days - 6 nights
Italy:
Northern Sardinia
+2 travellers
have booked
€850
Per person
4.9
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
+33 travellers
have booked
€846
€940
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
10907 reviews
25 April - 4 days sailing between La Maddalena and Bonifacio
05/3/2024
Bart S.
-
Spain
Sailing, early sun and aperitif at sunset ... What else?
05/3/2024
Cristiana L.
-
Italy
May 1st on Elba - Stewardess on board -3 Cab./ 3 Bathrooms
05/2/2024
susanna s.
-
Italy
25 April - Whale watching expedition with WWF researcher in Liguria
05/2/2024
Rossella D.
-
Italy
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