
Yacht sailing holidays & skippered tours in Italy
Discover more than 18 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
18
experiences

5.0
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
October - November
€350
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: Tuscany
3 days - 2 nights
One departure available
October - November
€390
€350
Per person

5.0
Italy: Venice and the Gulf of Trieste
1 day - 0 nights
One departure available
November
€99
Per person

3.0
Italy: Aeolian Islands
6 days - 6 nights
One departure available
November
€600
Per person

Italy: Liguria
1 day - 0 nights
16 departures available
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
One departure available
October
€110
Per person

Italy: Tuscany
1 day - 0 nights
5 departures available
November
Starting from
€115
Per person

5.0
Italy: Tuscany
2 days - 2 nights
5 departures available
October - November
Starting from
€220
€198
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
13747 reviews
North-East Sardinia and South Corsica on a sailing boat with gourmet cuisine
10/25/2025
Teresa B.
-
Germany
Barcolana weekend in Trieste and surroundings.
10/24/2025
Marilisa V.
-
Italy
Weekend in Capraia, the island with timeless sunsets
10/22/2025
D. D.
-
Italy
Relaxing weekend between Portovenere and the 5 Terre
10/21/2025
Manuela S.
-
Italy
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