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Yacht sailing holidays & skippered tours in Italy

Discover more than 22 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!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

August - October

Starting from

€600

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

4 departures available

August - September

Starting from

€689

Per person

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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

September

Starting from

€625

Per person

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4.9

Super!

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

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

September

Starting from

€200

€180

Per person

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4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

2 departures available

September

Starting from

€430

€409

Per person

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4.9

Super!

Taste of the sea between the island of Capraia and Northern Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

August - September

Starting from

€700

Per person

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4.9

Super!

Life-changing experiences: Four days in the Pontine Islands with photographer on board

Italy: Pontine Islands

4 days - 3 nights

3 departures available

September

Starting from

€450

€428

Per person

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5.0

Super!

South Sardinia

Italy: Southern Sardinia

6 days - 7 nights

4 departures available

August - September

Starting from

€790

€751

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

August - September

Starting from

€793

€714

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

4 departures available

September

Starting from

€430

€409

Per person

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4.9

Between seas and volcanoes, fall in love with the Aeolian Islands

Italy: Aeolian Islands

5 days - 4 nights

4 departures available

September

Starting from

€590

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

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

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 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

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

13737 reviews

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Barcolana 57: a day at the most famous regatta in the world

10/13/2025

Alessandro Marco B.

-

Italy

All very nice. Antonio was an excellent skipper, very nice and helpful. Super crew! To be redone
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Liguria sailing

10/13/2025

anna m.

-

Switzerland

I spent three wonderful days on Marco's boat! Marco is an exceptional skipper: attentive, competent and able to immediately understand those who wanted to learn to sail and those who simply wanted to relax and enjoy the sea. The company was cheerful and engaging, and in a few hours a very special atmosphere of harmony and understanding was created. It is the skipper who makes the difference, and Marco has been able to grasp and satisfy everyone's needs, making this experience unforgettable."
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The sea and sailing in autumn: two days on Elba

10/13/2025

Roberto T.

-

Italy

Ivo is a professional skipper. We had a technical outing that was very formative for me and we had fun.
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Poetic Gulf of Poets

10/9/2025

Massimo G.

-

Italy

Giovanni is a professional at his job,.. Expert, and collaborative with his customers... ADVICE....

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