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.
226
experiences
226
experiences
5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
August
€900
Per person
4.6
Italy: Pontine Islands
7 days - 7 nights
5 departures available
July - September
Starting from
€719
Per person
4.8
Super!
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
August
€1,190
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
5 departures available
July - September
Starting from
€650
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
5.0
Super!
Italy: Northern Sardinia
7 days - 7 nights
3 departures available
July - August
Starting from
€900
€810
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
7 departures available
July - September
Starting from
€690
€621
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
8 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
5.0
Super!
Italy: Tuscany
2 days - 2 nights
5 departures available
July - September
Starting from
€293
€264
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
July - August
Starting from
€780
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 - Private yacht sailing holidays with skipper in Italy
1563 reviews
Weekend only four guests - Elba Island
07/9/2025
Paola F.
-
Italy
Sailing weekend in the Pontine Islands
07/9/2025
Antonio F.
-
Italy
Between seas and volcanoes, fall in love with the Aeolian Islands
07/8/2025
Marco C.
-
Italy
Capri LightBlue and Positano BluSKy
07/8/2025
Marianna D.
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