Yacht sailing holidays & skippered tours in Italy
Discover more than 9 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
9
experiences
9
experiences
4.9
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
November
€299
Per person
4.8
Super!
Italy: Tuscany
3 days - 2 nights
One departure available
October - November
€260
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
November
€190
Per person
4.9
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€420
Per person
4.9
Italy: Aeolian Islands
7 days - 7 nights
One departure available
November
Starting from
€650
€585
Per person
3.0
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
4.1
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.
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
13167 reviews
Sardinia and Corsica on comfortable 15-metre boat with private bathroom in cabin
08/22/2025
Silvia R.
-
Italy
Lampedusa, Linosa and Lampione, islands on the high seas
08/22/2025
Manuela B.
-
Italy
Different Flotilla: Party and new friends in the Aeolian Islands
08/22/2025
Elga C.
-
Italy
The Wild Flotilla: dive into the wild nature of Tuscany and Corsica
08/21/2025
Benedetta M.
-
Italy
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