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.
110
experiences
110
experiences
4.8
Super!
Italy: Aegadian islands
7 days - 7 nights
3 departures available
September - October
Starting from
€950
Per person
4.8
Super!
Italy: Aeolian Islands
6 days - 7 nights
2 departures available
August - September
Starting from
€690
€529
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August - September
€750
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
September - October
€690
Per person
4.6
Italy: Northern Sardinia
6 days - 7 nights
2 departures available
September
Starting from
€750
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
September - November
€583
Per person
4.7
Italy: Northern Sardinia
6 days - 7 nights
One departure available
September
€901
Per person
5.0
Italy: Pontine Islands
4 days - 3 nights
2 departures available
September
Starting from
€450
Per person
4.7
Italy: Pantelleria and Lampedusa
6 days - 7 nights
5 departures available
August - October
Starting from
€930
€700
Per person
4.8
Italy: Aeolian Islands
6 days - 7 nights
2 departures available
September
Starting from
€950
€760
Per person - min 2 pax
5.0
Italy: Pontine Islands
3 days - 2 nights
3 departures available
September
Starting from
€420
Per person
4.7
Italy: Tuscany
7 days - 6 nights
3 departures available
September
Starting from
€600
Per person
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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
2269 reviews
4 days in the Pontine Islands (sailing school)
08/29/2025
Valentina M.
-
Italy
Sardinia and Corsica on comfortable 15-metre boat with private bathroom in cabin
08/29/2025
Giulia G.
-
Italy
Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew
08/29/2025
Silvia M.
-
Italy
Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation
08/29/2025
lara r.
-
Italy
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