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.
205
experiences
205
experiences
4.8
Super!
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
August
€1,190
Per person
4.6
Italy: Pontine Islands
7 days - 7 nights
3 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
4.9
Super!
Italy: Liguria
3 days - 2 nights
2 departures available
August - October
Starting from
€200
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
3 departures available
August
Starting from
€790
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
August - September
Starting from
€650
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: Aeolian Islands
7 days - 7 nights
7 departures available
July - October
Starting from
€751
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
8 days - 7 nights
One departure available
August - September
€660
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
August - September
Starting from
€583
€525
Per person
5.0
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
September
€293
€264
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
July - August
Starting from
€935
€748
Per person
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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
1619 reviews
Life-changing experiences - Escape to the Pontine Islands
07/15/2025
Anna R.
-
Italy
Weekend on Elba Island
07/15/2025
Dalgisa B.
-
Italy
Long weekend among the queens of the archipelago - Elba and Capraia
07/15/2025
Laurence B.
-
Belgium
Whale watching mini-cruise with WWF guide between Liguria and the French Riviera
07/15/2025
Tecla V.
-
Italy
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