Yacht sailing holidays & skippered tours in Italy
Discover more than 8 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
8
experiences
8
experiences
5.0
Italy: Aeolian Islands
7 days - 7 nights
One departure available
November
Starting from
€650
€585
Per person
4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
November
Starting from
€590
Per person
4.9
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
November
€299
Per person
4.9
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€420
Per person
Italy: Aeolian Islands
6 days - 6 nights
One departure available
November
Starting from
€600
Per person
Italy: Tuscany
1 day - 0 nights
7 departures available
October - November
Starting from
€115
Per person
4.2
Italy: Liguria
2 days - 1 night
5 departures available
November
€250
Per person
4.0
Italy: Sicily
6 days - 7 nights
5 departures available
November - December
€625
Per person
Why book a holiday with Sailsquare?
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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.
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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
12449 reviews
A day on a sailing boat to Gallinara Island or the Dianese Gulf
07/1/2025
Roberta M.
-
Italy
Sailing dreams in the Gulf of Poets and Cinque Terre
07/1/2025
Silvia S.
A weekend in the most beautiful coves of Elba
07/1/2025
Lucia F.
-
Italy
Relaxing weekend in the Pontine Islands
07/1/2025
Fabio D.
-
Italy
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