
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

New
Italy: Tuscany
1 day - 0 nights
7 departures available
November - December
€125
Per person
4.1
Italy: Tuscany
2 days - 2 nights
4 departures available
December
Starting from
€275
€248
Per person
4.1
Italy: Tuscany
4 days - 4 nights
4 departures available
November - December
€1,400
Per person

4.8
Italy: Naples & Amalfi Coast
5 days - 4 nights
One departure available
December - January
€570
Per person

New
Italy: Liguria
1 day - 0 nights
3 departures available
November
€75
Per person

5.0
Italy: Naples & Amalfi Coast
1 day - 0 nights
5 departures available
November - December
€100
Per person

4.7
Italy: Tuscany
5 days - 5 nights
One departure available
December - January
€400
Per person

5.0
New
Italy: Liguria
4 days - 3 nights
One departure available
December
€320
€288
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
15148 reviews
Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!
11/3/2026
Paolo P.
-
IT
Squid Festival 2026! - Capraia Isola
11/3/2026
Andrea C.
-
IT
Squid Regatta
10/20/2026
Valentina M.
-
IT
It's time for sun and sea!
10/19/2026
Francesco G.
-
IT
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