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2035144220

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

4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,190

Per person

4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - September

Starting from

€719

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

€900

Per person

4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

August - October

Starting from

€200

Per person

4.9

Super!

Week of sea, nature and fun in the Egadi Islands!

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August

Starting from

€790

Per person

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August - September

Starting from

€650

Per person

4.7

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€650

Per person

4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

July - October

Starting from

€751

Per person

4.8

Super!

From the Pontine to the Amalfi Coast by sailboat

Italy: Naples & Amalfi Coast

8 days - 7 nights

One departure available

August - September

€660

Per person

4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€583

€525

Per person

5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

September

€293

€264

Per person

5.0

Super!

Aeolian Islands - A week on a sailing boat with skipper and assistant

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€935

€748

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

1619 reviews

Life-changing experiences - Escape to the Pontine Islands

07/15/2025

Anna R.

Italy

Francesco super! Ponza and palmarola spendid. I celebrated a memorable birthday.

Weekend on Elba Island

07/15/2025

Dalgisa B.

Italy

We had a wonderful experience with a really good, competent and nice skipper, definitely to be repeated.

Long weekend among the queens of the archipelago - Elba and Capraia

07/15/2025

Laurence B.

Belgium

My partner had a terrific time on this trip - Edoardo is a knowledgeable, patient, and welcoming skipper. We also loved the beautiful scenery and the crew. The boat was perfect for a group of eight. We highly recommend a long weekend trip with Edoardo and Sailsquare.

Whale watching mini-cruise with WWF guide between Liguria and the French Riviera

07/15/2025

Tecla V.

Italy

Very nice and competent WWF skipper and popularizer. Pleasant trip. travel companions too I don't give 5 stars for the simple fact that on the poster presenting the trip it was written return at 4 pm on Sunday, while in reality the trip ended in the morning at 9., and having known it I would have organized myself better with the means of transport.

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