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Yacht sailing holidays & skippered tours in Italy

Discover more than 62 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!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

4 departures available

October

Starting from

€337

Per person

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4.8

Super!

Let's discover the Aeolian Islands together in Vela

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€690

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

October - November

€583

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

5 departures available

September - October

Starting from

€337

Per person

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4.7

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

3 departures available

October

€200

Per person

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4.8

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

October

Starting from

€200

€180

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

October

Starting from

€220

Per person

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4.8

Super!

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

October

€299

Per person

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4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

October

Starting from

€294

Per person

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5.0

Super!

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

2 departures available

September - October

€99

Per person

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5.0

Super!

Weekend Garda Lake 

Italy: Lake Garda

2 days - 2 nights

One departure available

October

€179

Per person

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5.0

Super!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

2 departures available

October

Starting from

€59

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

13641 reviews

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

09/17/2025

Mauro Z.

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Italy

Very nice cruise, despite the weather was not favorable, the skipper managed to let us enjoy the beauties of the Costa Smeralda
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Weekend at the Pontine aboard a splendid 16-meter sailboat

09/17/2025

Giulia E.

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Italy

It was my first time on a sailing boat but the skipper Leonardo and his wife Elena were immediately very professional and attentive to everyone's needs. The boat is very nice, functional and clean; perfect for enjoying the sea in total relaxation. The excellent company, the favorable weather and the crystal clear water of the Pontine islands then made the experience perfect!
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Egadi paradise for sailing and snorkeling

09/17/2025

Vicky H.

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Belgium

Mario is a competent and friendly skipper. The Egadi islands are beautiful and the boat is in good shape. It is a pity that 2 French-speaking fellow passengers had a lot of criticism, made little effort to involve the skipper in the conversations and were very present during the trip, to the displeasure of the other passengers.
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A week in the Aeolian Islands - 6 islands in seven days

09/17/2025

Giuseppe I.

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Italy

The sailing trip with Nicola was an experience that enriched me a lot, unique emotions and sensations. The navigation, the wind, the sun and the sea created a perfect mix of adventure and relaxation. I recommend everyone to try this experience at least once in their life: it is an opportunity to discover the beauty of the sea, the Aeolian Islands and the feeling of freedom. Thanks to all the crew, who made all this possible.

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