
Yacht sailing holidays & skippered tours in Italy
Discover more than 42 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
42
experiences

4.6
Premium
Italy: Northern Sardinia
7 days - 7 nights
5 departures available
October - November
Starting from
€1,640
€1,558
Per person - min 2 pax

4.7
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
October
Starting from
€590
Per person

4.9
Italy: Aegadian islands
7 days - 7 nights
One departure available
October
Starting from
€950
€855
Per person

4.7
Italy: Naples & Amalfi Coast
2 days - 2 nights
4 departures available
October
Starting from
€275
Per person

5.0
Super!
Italy: Liguria
2 days - 1 night
2 departures available
October
€220
Per person
4.1
Italy: Tuscany
2 days - 2 nights
5 departures available
October - November
Starting from
€300
€270
Per person

4.4
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
October
Starting from
€540
€513
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
October
Starting from
€230
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
October
Starting from
€230
Per person

4.6
Italy: Northern Sardinia
6 days - 7 nights
One departure available
September - October
Starting from
€650
€585
Per person

4.8
Italy: Aeolian Islands
7 days - 7 nights
One departure available
October
Starting from
€750
€675
Per person

New
Italy: Pantelleria and Lampedusa
7 days - 7 nights
4 departures available
October - November
Starting from
€500
€348
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
14253 reviews
A week in the Aeolian Islands - 6 islands in seven days
07/23/2026
Deborah T.
-
IT
Week end in Costa Azzurra
07/23/2026
Isabella R.
-
IT
The magic of the Egadi Islands aboard a brand new catamaran
07/23/2026
Maurizio D.
-
IT
Authentic Aeolian Islands on a sailboat: between local flavors and crystal clear sea
07/22/2026
chiara a.
-
IT
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