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Yacht sailing holidays & skippered tours in Italy

Discover more than 42 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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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

October

Starting from

€200

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€751

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

October

Starting from

€615

Per person

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4.8

Super!

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

2 departures available

October

Starting from

€850

€808

Per person

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5.0

Super!

Experience in the Egadi Islands: A Dream on a Sailing Boat

Italy: Aegadian islands

7 days - 7 nights

3 departures available

October

Starting from

€400

€360

Per person

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4.8

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

One departure available

September - October

Starting from

€240

€228

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

Midweek relaxing in the Pontine Mountains

Italy: Pontine Islands

4 days - 3 nights

5 departures available

September - October

Starting from

€337

Per person

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5.0

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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4.2

Stuffed anchovies: magical weekend from Genoa

Italy: Liguria

2 days - 2 nights

2 departures available

October

Starting from

€265

Per person

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4.7

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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5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

One departure available

September

Starting from

€99

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

12594 reviews

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ENJOY: in the blue painted blue of the Aeolian Islands

07/17/2025

Ellis M.

-

Germany

A fantastic experience and trip, thanks to the wonderful skipper/chef Matteo!
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Weekend sailing in the Pontine Islands

07/17/2025

Claudio R.

-

Italy

Fabulous first sailing experience, thanks to the presence of Claudio as skipper. Friendliness, flexibility, tips and culinary skills that allow you to fully enjoy your days on board. Functional and comfortable boat, especially with non-maximum capacity.
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Set Sail with Family: 5 Days of Comfort & Adventure Around Elba Island

07/17/2025

LARA A.

-

Italy

An unforgettable experience. The holiday, although short, was really fun, relaxing, and above all it served to make us understand how much we love being on the boat, and therefore we will definitely do it again. The captain was fantastic, he always kept the whole crew happy, he proposed and shared with all the guests experiences and moments that we will not forget. Matteo is absolutely professional and attentive to everything, as well as nice. He also has a lot of patience with children, so I rate 5 stars! I recommend this experience to anyone who wants to try sailing with children. Thank you Matteo and thanks to Sailsquare for the professionalism and punctuality shown. Good bye Lara
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The pearls of Liguria: Portoverne, Lerici and the Gulf of Poets

07/16/2025

Federica P.

-

Italy

totally agree with what Simone T. wrote.

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