Yacht sailing holidays & skippered tours in Italy
Discover more than 153 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
153
experiences
153
experiences
4.5
Duration:
7 days - 7 nights
Italy:
Tuscany
Give this experience a try!
€1,350
Per person
Duration:
2 days - 1 night
Italy:
Liguria
Give this experience a try!
€199
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Gulf of Naples
Give this experience a try!
€200
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Liguria
+12 travellers
have booked
Starting from
€332
€390
Per person
4.7
Duration:
2 days - 2 nights
Italy:
Gulf of Naples
Give this experience a try!
€225
Per person
4.8
Duration:
3 days - 3 nights
Italy:
Tuscany
Give this experience a try!
Starting from
€324
€360
Per person
Duration:
2 days - 2 nights
Italy:
Liguria
+21 travellers
have booked
€380
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Liguria
chiara c.
has booked
Starting from
€95
Per person
5.0
Duration:
2 days - 1 night
Italy:
Pontine Islands
Give this experience a try!
€220
Per person
Duration:
1 day - 0 nights
Italy:
Liguria
Give this experience a try!
Starting from
€162
€170
Per person
4.5
Duration:
2 days - 1 night
Italy:
Liguria
Give this experience a try!
€230
Per person
5.0
Duration:
2 days - 1 night
Italy:
Venice and the Gulf of Trieste
Give this experience a try!
€188
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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