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Yacht sailing holidays & skippered tours in Italy

Discover more than 222 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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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,190

Per person

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4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€719

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€900

Per person

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4.7

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

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August - September

Starting from

€650

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

August

Starting from

€200

Per person

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4.9

Super!

Week of sea, nature and fun in the Egadi Islands!

Italy: Aegadian islands

7 days - 7 nights

4 departures available

August - September

Starting from

€690

€621

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

3 departures available

August - September

Starting from

€650

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€751

Per person

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4.8

Super!

From the Pontine to the Amalfi Coast by sailboat

Italy: Naples & Amalfi Coast

8 days - 7 nights

One departure available

August - September

€660

Per person

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4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

7 days - 7 nights

One departure available

August

Starting from

€583

€525

Per person

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5.0

Super!

Aeolian Islands - A week on a sailing boat with skipper and assistant

Italy: Aeolian Islands

7 days - 7 nights

One departure available

August

Starting from

€935

€748

Per person

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4.8

Super!

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€820

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

12570 reviews

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Escape from the city for a weekend of sea and relaxation

07/14/2025

Francesco T.

-

Italy

Clean, new boat complete with all equipment. Carlo the skipper is a very kind and prepared person. Beautiful bbq evening on the boat.
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Egadi Islands & San Vito Lo Capo - Blue Transparency!

07/14/2025

TATIANA CRISTIANA D.

-

Italy

Francesco is a highly qualified skipper who has a great command in driving the sailboat, in doing all the necessary maneuvers with great promptness and safety. Sailing with him is a certainty, absolutely recommended.
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North Sardinia and South Corsica by catamaran with flybridge

07/14/2025

francesca f.

-

Italy

The boat was very nice, comfortable and spacious. The environment is clean. The kitchen is large and comfortable. The only drawback: this type of boat does not offer great fun while sailing because it is not always possible to hoist the sails... Comfort is preferred to sailing. Antonio was a very good skipper, careful to meet the multiple needs of the whole crew. He made us discover wonderful places that will remain in our hearts.
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Week between the Tuscan Islands and North Corsica

07/14/2025

Flavia G.

-

Italy

Francesco is an experienced skipper, skilled in managing the unexpected and meeting the needs of the whole crew. The boat is comfortable and equipped with everything you need to spend a pleasant holiday.

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