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Yacht sailing holidays & skippered tours in Italy

Discover more than 206 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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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

July - August

Starting from

€750

€675

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

July - August

Starting from

€590

Per person

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4.6

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

3 departures available

July

Starting from

€1,640

€1,558

Per person - min 2 pax

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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

2 departures available

July - August

Starting from

€950

Per person

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4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

July

€390

€351

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

One departure available

July - August

Starting from

€795

€716

Per person

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4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

July - August

Starting from

€620

€558

Per person

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4.6

Long weekend between Ponza and Palmarola: adventure at the Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

Per person

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4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

One departure available

July

Starting from

€1,052

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

2 departures available

June - July

Starting from

€950

€855

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€689

Per person

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5.0

Super!

Weekend at the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€350

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 - Yacht sailing holidays & skippered tours in Italy

13922 reviews

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Weekend of sea and colors between Ischia, Procida and Vivara

06/17/2026

Domenico T.

This was my first boat adventure and what an adventure, starting from the boat which is much more spacious than I expected, passing to Emiliano, the skipper, who with his professionalism and sympathy explained the rudiments of navigation and finally the location, Ischia and Procida, which are a spectacle of Campania.

Weekend of sea and colors between Ischia, Procida and Vivara

06/17/2026

Domenico R.

Beautiful sailing experience between Naples, Ischia and Procida. Emiliano is a kind and helpful skipper who manages to make the experience special, actively involving those who want to feel part of the crew. Highly recommended!

Weekend of sea and colors between Ischia, Procida and Vivara

06/17/2026

Sabrina C.

I left for a weekend with "Spasso a vela" and it was an unforgettable experience. The boat is very comfortable, equipped with all possible amenities, it is very spacious, the cabins are comfortable and the 3 bathrooms on board are more than enough to feel comfortable. During our weekend we encountered slightly rough seas and a bit of wind but despite this thanks to the skipper's navigation experience, both in managing the navigation and in finding strategic points to dock, the weather conditions that were not entirely favorable did not weigh on us at all, so we fully enjoyed the beautiful landscapes and the sea. It was also super interesting to participate actively in life on board, the skipper taught us a lot of notions and involved us in the maneuvers. It is an experience that I recommend and that I will definitely return to do with "Spasso a vela".

A taste of the magnificent Island of Elba

06/17/2026

valentina t.

-

IT

We with friends at the Top! The boat very clean and welcoming, Alberto always on the piece helpful and attentive.

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