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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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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 - 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

5 departures available

July - 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 - September

Starting from

€950

Per person

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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 - September

Starting from

€600

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 - September

Starting from

€600

€540

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

5 departures available

July - August

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

5 departures available

August - September

Starting from

€700

Per person

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5.0

Super!

A bordo con lo chef alle Egadi

Italy: Aegadian islands

7 days - 7 nights

5 departures available

August - September

Starting from

€800

€720

Per person

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5.0

Super!

South Sardinia

Italy: Southern Sardinia

6 days - 7 nights

5 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

5 departures available

August - September

Starting from

€793

€714

Per person

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4.7

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

5 departures available

July - August

Starting from

€200

€180

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

3 departures available

July - August

Starting from

€430

€409

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

13744 reviews

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Relaxing weekend between Portovenere and the 5 Terre

10/21/2025

Manuela S.

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Italy

Fully satisfied Advice to live a unique experience.
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A day sailing in the fantastic Gulf of Trieste

10/20/2025

Monica C.

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Italy

The skipper Paolo simply fabulous. The super cozy and high-performance boat. We had a beautiful, immersive experience and learned even a minimum basis of sailing concepts
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We have known the Aeolian Islands for 20 years. - Live them with us.

10/20/2025

Marco F.

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Italy

Pasquale is a profound lover and connoisseur of the Aeolian Islands. Beyond the experience at sea, it also suggests excursions and places to visit on land
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Fantastic BARCOLANA: Racing in safety and joy!

10/15/2025

Giulia B.

-

Italy

Beautiful experience with nice and heterogeneous crew! Paolo is a professional person who guided and taught us, transmitting his passion for sailing. Advised!

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