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Yacht sailing holidays & skippered tours in Italy

Discover more than 59 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!

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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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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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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4.9

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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4.6

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

October - November

Starting from

€1,455

€1,382

Per person

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4.9

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

October

Starting from

€275

€248

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

€363

€290

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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4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

One departure available

October

Starting from

€930

€700

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

Starting from

€99

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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4.9

Super!

Weekend catamaran in Portovenere and Cinque Terre

Italy: Liguria

3 days - 2 nights

One departure available

October

€225

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

13484 reviews

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Weekend only four guests - Elba Island

09/4/2025

Benedetta F.

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Italy

We had a fantastic weekend in Elba! The boat is comfortable and welcoming; Pier Paolo was available in proposing the best itinerary based on the weather and our needs and in letting us participate in the sailing maneuvers, making us protagonists of the experience. I highly recommend it and hope to be back on board soon!
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Summer 2025 - Catamaran week in the Pontine Islands

09/4/2025

Barbara C.

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Italy

Overall well managed, total availability towards the needs of guests
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ONE WAY From the Phlegraean to the Pontine Islands

09/4/2025

Eugenia C.

-

Italy

The boat would need a little more extraordinary maintenance. Super professionally trained skipper, overall very nice holiday I met people with whom I was able to share so many things.
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Between seas and volcanoes, fall in love with the Aeolian Islands

09/3/2025

Rocco P.

-

Italy

Positive experience, Antonio is a prepared and condescending skipper always calm in every situation who prefers the roadstead to the ports, with him in the Aeolian Islands you are on the safe side!

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