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Yacht sailing holidays & skippered tours in Italy

Discover more than 45 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

October - November

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

One departure available

October

Starting from

€950

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

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4.8

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

Starting from

€750

€675

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

5 departures available

October - November

€300

€270

Per person

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4.0

New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

2 departures available

October - November

€500

€348

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

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

4 departures available

October

Starting from

€230

Per person

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4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

One departure available

October

Starting from

€860

Per person

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4.4

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October

Starting from

€540

€513

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

4 departures available

October

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.

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 - Yacht sailing holidays & skippered tours in Italy

14436 reviews

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2 boats in Costa Smeralda and Bonifacio aboard a 16-meter traditional sailing yacht.

08/9/2026

Claudia D.

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IT

Super experience: relaxation, fun, safety, passion and so much to learn. Sailing with Vico is a guarantee! He has a very unique enthusiasm for sailing. He doesn't just set the course, but loves to share what he knows, explain the maneuvers and let those who want to get at the helm or the sheets try. Unforgettable days!
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Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

08/9/2026

Silvia S.

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IT

For the second year we chose the Pontine with the same boat. Lovely places!
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/9/2026

Fabio Valerio R.

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CH

Very bad. Extremely expensive overall. Nice place but bad organization. Reluctantly not recommended. Hard to thank .

Sailing holiday in the turquoise blue waters of Corsica

08/9/2026

Fedra M.

-

IT

Experience above expectations. The crew made us feel comfortable right away. He delighted us with great food and good company. It involved us in the experience of sailing which was exciting!!

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