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Yacht sailing holidays & skippered tours in Italy

Discover more than 163 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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4.8

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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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August - October

Starting from

€950

Per person

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4.8

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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4.7

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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4.8

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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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

August - October

Starting from

€690

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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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

One departure available

August - September

Starting from

€1,150

€1,035

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

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

3 departures available

August - September

Starting from

€790

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

3 departures available

September

Starting from

€230

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.

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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

14129 reviews

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Positano, Amalfi and Capri by Catamaran

07/11/2026

Claudio Alessandro S.

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IT

Skipper top
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Mini whale watching cruise with WWF guide between Ponza and Palmarola

07/11/2026

beatrice c.

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IT

The trip exceeded my expectations thanks to Luca and Andrea. Andrea, our naturalist guide was always available at any time for any curiosity of the group, competent in the subject, generous, with remarkable soft skills, a serious young man, intelligent educated a reliable professional with great psychological balance. Luca, our skipper was a firm point, skilled, safe always attentive to our personal safety and to the boat, wise, polite, direct and directive the right: truly a great leader! Luca and Andrea are a couple that works very well, they know how to work in a synergistic, harmonious way, this makes them highly reliable, moreover excellent listeners and also funny!! With them I would go anywhere, relying on myself completely. I found the boat a bit too old and uncomfortable for 10 people, in my opinion Luca and Andrea and another person had to adapt a lot, even if I never heard a complaint from them. I thank you for all the welcome I received and for the joy I experienced.

4 Days Argentario-Giannutri-Giglio-Talamone

07/11/2026

Francesca M.

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IT

Tommy is a competent and easygoing skipper! He accompanied us on our first multi-day boat holiday with relaxation, irony and great availability. We met her wonderful family: Sofia and their magnificent "Leonidas"! Thank you for everything. See you next time!!

Midweek getaway between Elba and Capraia

07/11/2026

Simona S.

-

IT

Beautiful and highly recommended experience. A real escape from everyday life, to rediscover beauty and slow rhythms. Marco welcoming, nice and safe. Top.

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