Private yacht sailing holidays with skipper in Italy
Chartering a sailing boat in Italy will let you discover a new way of travelling new way of travelling in complete freedom. Choose between a catamaran or a sailing boat and embark with an experienced skipper to discover Tuscany, Sicily, Tuscany, Sicily, Sardinia and many other destinations.
220
experiences
220
experiences
4.8
Super!
Italy: Northern Sardinia
7 days - 7 nights
One departure available
August
€1,190
Per person
4.6
Italy: Pontine Islands
7 days - 7 nights
4 departures available
July - September
Starting from
€719
Per person
5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
August
€900
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
5 departures available
July - September
Starting from
€650
Per person
5.0
Super!
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
July - August
Starting from
€900
€810
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
2 departures available
August - October
Starting from
€200
Per person
4.7
Italy: Northern Sardinia
6 days - 7 nights
8 departures available
July - September
Starting from
€650
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
5 departures available
August - September
Starting from
€690
€621
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August
€820
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
7 departures available
July - October
Starting from
€751
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
July - August
Starting from
€935
€748
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
September
Starting from
€583
€525
Per person
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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 - Private yacht sailing holidays with skipper in Italy
1567 reviews
Short sailing cruise in the Gulf of Naples
07/11/2025
Daniela D.
-
Italy
Life-changing experiences - Escape to the Pontine Islands
07/11/2025
Emanuela P.
Sailing weekend in the Pontine Islands
07/10/2025
Stefano M.
-
Italy
Dream sailing on a fully-equipped catamaran
07/9/2025
Alessandro B.
-
Italy
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