
Yacht sailing holidays & skippered tours in Italy
Discover more than 212 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
212
experiences

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
July - August
Starting from
€700
Per person

4.8
Super!
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
€1,125
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: 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
€600
€570
Per person

4.7
Italy: Naples & Amalfi Coast
3 days - 3 nights
2 departures available
June - July
Starting from
€390
€351
Per person

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

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

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
July - August
Starting from
€690
Per person

4.7
Italy: Tuscany
6 days - 6 nights
One departure available
July
Starting from
€1,052
Per person
4.6
Italy: Tuscany
2 days - 2 nights
2 departures available
July
Starting from
€300
€270
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
13883 reviews
Summer is made for the Aeolian Islands! Weekly cruise
06/11/2026
Patrizia R.
-
IT
June 2 - cetacean watching expedition in the Pelagos Sanctuary with WWF guide
06/10/2026
Guido F.
-
IT
Weekend in Ischia and Ventotene: History and Nature
06/10/2026
Michele F.
-
IT
June 2nd long weekend between Ponza, Palmarola, Zannone and Ventotene
06/10/2026
Donatella L.
-
IT
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