Yacht sailing holidays & skippered tours in Italy
Discover more than 238 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
238
experiences
238
experiences
Duration:
6 days - 7 nights
Italy:
Pantelleria and Lampedusa
Give this experience a try!
€800
Per person
Duration:
5 days - 6 nights
Italy:
Aegadian islands
Give this experience a try!
€900
Per person
4.6
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
Give this experience a try!
€850
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+12 travellers
have booked
Starting from
€551
€580
Per person
4.6
Duration:
7 days - 6 nights
Italy:
Pontine Islands
Give this experience a try!
Starting from
€700
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
Give this experience a try!
€1,000
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+6 travellers
have booked
Starting from
€425
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+3 travellers
have booked
€1,000
Per person
4.7
Duration:
6 days - 7 nights
Italy:
Campania
+16 travellers
have booked
Starting from
€690
Per person
5.0
Duration:
8 days - 8 nights
Italy:
Sicily
Give this experience a try!
€799
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+41 travellers
have booked
Starting from
€799
Per person
4.6
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+4 travellers
have booked
Starting from
€519
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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