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Yacht sailing holidays & skippered tours in Italy

Discover more than 153 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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4.6

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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4.7

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

Per person

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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

August - October

Starting from

€950

€855

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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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August - October

Starting from

€590

Per person

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4.8

Super!

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

Italy: Tuscany

6 days - 7 nights

One departure available

August - September

Starting from

€900

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

€1,041

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

Starting from

€950

Per person

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5.0

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

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - October

Starting from

€690

Per person

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

2 departures available

August - September

€220

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

€1,150

€1,035

Per person

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4.8

Super!

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

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

August - September

Starting from

€583

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

14282 reviews

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Sailing from Tuscany to South Corsica

07/26/2026

Serena P.

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IT

Beautiful experience, super comfortable boat, brilliant and knowledgeable skipper took us to beautiful places and sailing with the wind in our sails ,!! To be done again bye Marco
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Aeolian Islands: sun, sport, music, good food... The rest is magic!

07/26/2026

Benedetto R.

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IT

Great skipper Captain Dario, professional and precise in the management and management of his [hidden]. It makes you feel immediately at ease in a boat equipped with every comfort. I hope to see you again soon at sea. Fair Winds 🌬️ greetings Benedict

Aeolian Islands: sun, sport, music, good food... The rest is magic!

07/26/2026

Camilla V.

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IT

Experience to be redone! A group of nice people and a professional skipper who over time has made himself loved 😂❤️ We recommend everyone a nice week in the Aeolian Islands with the [hidden].

Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica

07/26/2026

Isaia N.

-

IT

It was an exciting and interesting experience.

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