Yacht sailing holidays & skippered tours in Italy
Discover more than 60 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
60
experiences
60
experiences
5.0
Duration:
1 day - 0 nights
Italy:
Lake Garda
+25 travellers
have booked
€99
Per person
Duration:
7 days - 7 nights
Italy:
Aegadian islands
Give this experience a try!
€299
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+4 travellers
have booked
€1,200
Per person
4.8
Duration:
3 days - 3 nights
Italy:
Tuscany
+7 travellers
have booked
€300
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€315
Per person
4.3
Duration:
3 days - 3 nights
Italy:
Tuscany
susanna s.
has booked
€399
Per person
4.8
Duration:
1 day - 0 nights
Italy:
Liguria
Give this experience a try!
€140
Per person
Duration:
6 days - 6 nights
Italy:
Aeolian Islands
+4 travellers
have booked
€650
Per person
4.9
Duration:
3 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€265
Per person
4.5
Duration:
3 days - 4 nights
Italy:
Tuscany
Elettra
has booked
€350
Per person
4.9
Duration:
5 days - 5 nights
Italy:
Pontine Islands
Give this experience a try!
€405
€450
Per person
4.9
Duration:
5 days - 5 nights
Italy:
Tuscany
Give this experience a try!
€618
€650
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
10894 reviews
A weekend of sailing between Capraia and the island of Elba
04/24/2024
Angelo C.
-
Italy
Easter on the Island of Elba
04/22/2024
Antonios S.
-
Italy
Trekking and sailing weekend on the island of Elba
04/22/2024
Sara C.
-
Italy
Luxury sailing in the Gulf of Poets
04/15/2024
Antonio C.
-
Italy
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