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Yacht sailing holidays & skippered tours in Italy

Discover more than 189 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!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August - September

Starting from

€680

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

August - September

Starting from

€590

Per person

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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

2 departures available

August - September

Starting from

€950

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

5 departures available

August - September

Starting from

€1,640

€1,558

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

August - September

Starting from

€550

€523

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

5 departures available

August - September

Starting from

€795

€716

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

3 departures available

August - September

Starting from

€689

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

3 departures available

August - September

Starting from

€950

€855

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

August

Starting from

€680

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

4 departures available

August - September

Starting from

€650

€585

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

3 departures available

August - September

Starting from

€999

€949

Per person

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4.7

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

3 departures available

August

Starting from

€300

€270

Per person

Why book a holiday with Sailsquare?

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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

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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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

13809 reviews

In the blue of Capri and the infinity of the Amalfi Coast

05/26/2026

Roberto L.

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IT

A great weekend! Beautiful places visited, particular attention was paid to organizing the tour in maximum safety in navigation and in maximum comfort. The skipper Gennaro is very prepared, a well-equipped boat, very comfortable and externally clean. Highly recommended
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Weekend Elba o Capraia

05/26/2026

Sabrina S.

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IT

Fantastic holiday with the guidance of Francesco who involved us a lot in managing the destination and the boat, taught us how the sea can create bonds.
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Weekend among the most beautiful coves of Elba

05/26/2026

Samantha G.

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IT

We were literally welcomed by Marco and Carmen, it seemed to have known them for a lifetime. Evidently they attract beautiful people because the rest of the crew was also wonderful. Beautiful sailings (you can move as little as possible), but managed in full comfort. Finally, an excellent knowledge of the places that does not hurt and makes you enjoy unforgettable coves
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Tuscan archipelago between nature and relaxation

05/26/2026

Francesco D.

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IT

Riccardo is a true professional, a reliable person and also an excellent travel companion. He was able to perfectly interpret our requests with availability and empathy, becoming in a few minutes a friend, an accomplice in adventures, a trusted person, as if we had always known each other ... Not just a skipper! Thanks to Riccardo and "[hidden]" for this wonderful experience!

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