Yacht sailing holidays & skippered tours in Italy
Discover more than 19 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
19
experiences
19
experiences
5.0
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
October - November
€320
Per person
4.9
Super!
Italy: Tuscany
3 days - 2 nights
One departure available
October - November
€310
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
€350
Per person
4.8
Italy: Tuscany
3 days - 3 nights
One departure available
November
€299
Per person
5.0
Italy: Venice and the Gulf of Trieste
1 day - 0 nights
One departure available
November
€99
Per person
4.9
Italy: Liguria
2 days - 2 nights
4 departures available
October - November
Starting from
€260
€247
Per person
3.0
Italy: Aeolian Islands
6 days - 6 nights
One departure available
November
€600
Per person
Italy: Liguria
1 day - 0 nights
18 departures available
October - November
€86
Per person
4.0
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€390
Per person
Italy: Naples & Amalfi Coast
1 day - 0 nights
3 departures available
October
€110
Per person
5.0
Italy: Tuscany
3 days - 2 nights
One departure available
October - November
€390
€351
Per person
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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
13745 reviews
Weekend in Capraia, the island with timeless sunsets
10/22/2025
Don D.
-
Italy
Relaxing weekend between Portovenere and the 5 Terre
10/21/2025
Manuela S.
-
Italy
A day sailing in the fantastic Gulf of Trieste
10/20/2025
Monica C.
-
Italy
We have known the Aeolian Islands for 20 years. - Live them with us.
10/20/2025
Marco F.
-
Italy
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