
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.
121
experiences

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

4.7
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
September - October
Starting from
€700
Per person

4.8
Super!
Italy: Tuscany
6 days - 7 nights
One departure available
August
€1,100
Per person

4.7
Italy: Pontine Islands
3 days - 3 nights
One departure available
September
€420
€378
Per person

5.0
Super!
Italy: Liguria
2 days - 1 night
One departure available
October
€220
Per person

4.8
Super!
Italy: Liguria
2 days - 2 nights
One departure available
August - September
€360
€324
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
One departure available
August - September
€950
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
September - October
Starting from
€750
€675
Per person

4.9
Super!
Italy: Liguria
3 days - 2 nights
One departure available
September
€280
Per person

5.0
Super!
Italy: Pontine Islands
5 days - 4 nights
One departure available
September
€550
Per person

5.0
Italy: Tuscany
3 days - 3 nights
3 departures available
August - September
Starting from
€350
Per person

4.8
Super!
Italy: Aegadian islands
6 days - 7 nights
One departure available
September
€1,100
Per person
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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.
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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
3271 reviews
Gargano National Park and Marine Protected Area of the Tremiti Islands
08/22/2026
Antonella B.
-
IT
Island of Elba and South Corsica fantastic week
08/22/2026
Myriam C.
-
IT
Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms
08/22/2026
Emanuele P.
-
IT
Flotilla Smeralda: La Maddalena Archipelago with Velasquez - MEN'S SEATS ONLY
08/22/2026
Luca A.
-
IT
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