
Yacht sailing holidays & skippered tours in Italy
Discover more than 206 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
206
experiences

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
July - August
Starting from
€750
€675
Per person

4.8
Italy: Northern Sardinia
6 days - 7 nights
2 departures available
July - August
Starting from
€590
Per person

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

4.9
Italy: Aegadian islands
7 days - 7 nights
2 departures available
July - August
Starting from
€950
Per person

4.7
Italy: Naples & Amalfi Coast
3 days - 3 nights
One departure available
July
€390
€351
Per person

4.7
Italy: Pontine Islands
7 days - 7 nights
One departure available
July - August
Starting from
€795
€716
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
July - August
Starting from
€620
€558
Per person

4.6
Italy: Pontine Islands
4 days - 3 nights
One departure available
July
€490
Per person

4.7
Italy: Tuscany
6 days - 6 nights
One departure available
July
Starting from
€1,052
Per person

5.0
Super!
Italy: Tuscany
6 days - 7 nights
2 departures available
June - July
Starting from
€950
€855
Per person

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
July - August
Starting from
€689
Per person

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
One departure available
July
€350
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
13922 reviews
Weekend of sea and colors between Ischia, Procida and Vivara
06/17/2026
Domenico T.
Weekend of sea and colors between Ischia, Procida and Vivara
06/17/2026
Domenico R.
Weekend of sea and colors between Ischia, Procida and Vivara
06/17/2026
Sabrina C.
A taste of the magnificent Island of Elba
06/17/2026
valentina t.
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