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.

236

experiences

4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€700

Per person

4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,070

Per person

4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€600

€570

Per person

4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

10 departures available

August - October

Starting from

€590

Per person

4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€795

Per person

4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

6 departures available

July - October

Starting from

€950

Per person

4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

2 departures available

August - September

Starting from

€1,041

Per person

4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,000

Per person

5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

3 departures available

August - September

Starting from

€1,150

€1,035

Per person

5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€1,100

Per person

4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

Starting from

€1,052

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

2832 reviews

All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

07/6/2026

Matteo D.

Beautiful and fun experience. Matteo proved to be very helpful and an experienced skipper and able to find solutions in any situation. Fantastic company and the other three skippers Claudio, Leo and Francesco good and very nice

Week end in Costa Azzurra

07/6/2026

Anna Rita V.

Very nice experience Very nice people Very helpful and professional skipper

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

07/6/2026

Ilaria M.

Riccardo was a fantastic skipper, both technically and humanly. Very nice and human. It was nice to share life experiences with him. He gave us a beautiful holiday that will remain in our memories. Great food, super super recommended!!

Magnificent weekend of approach to sailing on the island of Elba

07/6/2026

Egle R.

Thank you very much to Sandro ! Very kind person with big heart and with good sense of humor ! I'm really amused. Boat sail was nice, tidy and clean ! There are rules in the edge that makes so much sense to me and right. Sandro always asked us if we want to go or stop and etc. Pecatto we could not sail with sail, but unfortunately mother nature decided not to give wind, but everywhere everything was perfect and I am glad that climbed in the edge of Sandro! Thank you and good wind!

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