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Yacht sailing holidays & skippered tours in Italy

Discover more than 24 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 - October

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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4.8

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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4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

August - October

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

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

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

One departure available

September

Starting from

€272

Per person

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4.7

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

September

Starting from

€200

€180

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

13741 reviews

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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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Barcolana weekend in Trieste and surroundings.

10/15/2025

Barbara M.

-

Italy

MARINO fantastic skipper, he pampered us ( swim in the blue included), he was very helpful for all our whims. The Barcolana is a grandiose spectacle, seen from the sea it excites a lot, if you like sailing you can not avoid being there at least once. The kitten on board, Lightning is a very sweet travel companion. After the restyling in the shipyard, the catamaran will also be up to the task.
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Weekend in Capraia, the island with timeless sunsets

10/14/2025

Gloria G.

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Italy

Wonderful weekend. Super skipper! Very professional and helpful, he entertained us by telling us many curiosities about sailing and the places visited. The fantastic boat with ample space and equipped with everything you need! 100% recommended both the skipper and the destination!
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Barcolana 2025: experience the most beautiful regatta with me!

10/14/2025

Gabriele I.

-

Italy

Very good Gianni

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