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Yacht sailing holidays & skippered tours in Italy

Discover more than 160 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

2 departures available

August - September

Starting from

€700

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

August - October

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

5 departures available

August - October

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

5 departures available

August - October

Starting from

€950

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

August - September

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

One departure available

August - September

Starting from

€600

€570

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

One departure available

August - September

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

5 departures available

August - October

Starting from

€689

Per person

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4.7

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

Italy: Tuscany

6 days - 6 nights

One departure available

August - September

Starting from

€1,041

Per person

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4.7

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

September

Starting from

€300

€270

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

3 departures available

September

Starting from

€490

€466

Per person

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4.6

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

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August - October

Starting from

€650

€585

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.

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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 - Yacht sailing holidays & skippered tours in Italy

13861 reviews

Four days among the islands of the Gulf of Naples

06/8/2026

Eleonora S.

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IT

For our first catamaran experience we chose Angelo and his [hidden] and we couldn't have made a better choice! A helpful and experienced captain, who made us discover the most beautiful bays of Procida and Ischia. Together with him, the cook Diego who satisfied all our requests with incredible kindness! We are super satisfied and hope to leave soon with them! [hidden] is beautiful and very well-kept, convenient even for those who, like us, had no experience of boat holidays!
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Weekend of the Pontine Islands to discover Ponza and Palmarola

06/8/2026

Ilaria A.

Unforgettable experience! Marco and Giada are fantastic, attentive to everyone's needs, flexible and ready for any experience. The boat is home to it's nice to share every space. I wish you a journey like this, a journey of the soul between the waves of the sea and the waves of the wind.

Weekend of approach to sailing in the setting of the Gulf of Poets

06/8/2026

Chiara B.

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IT

Fantastic weekend and experience absolutely to be repeated. Thanks to Commander Sandro! See you next time!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

06/8/2026

Laura S.

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DE

Everything perfect - a particularly beautiful week

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