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Yacht sailing holidays & skippered tours in Italy

Discover more than 74 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

One departure available

June - July

Starting from

€700

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

One departure available

June - July

Starting from

€1,640

€1,558

Per person - min 2 pax

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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

June - July

Starting from

€950

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

One departure available

June - July

Starting from

€600

€570

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

One departure available

June - July

Starting from

€950

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

One departure available

June - July

Starting from

€690

Per person

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5.0

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

One departure available

June - July

Starting from

€790

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

One departure available

June

Starting from

€490

€466

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

June - July

Starting from

€700

Per person

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5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

June - July

Starting from

€900

€765

Per person

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5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

2 departures available

June

Starting from

€390

€351

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

2 departures available

June - July

Starting from

€490

Per person

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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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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

13941 reviews

Sail to the Aeolian Islands with an experienced crew on a catamaran!

06/21/2026

Barbara M.

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IT

We spent a super holiday visiting all the Aeolian Islands, captain Emanuele and skipper Daniele despite their young age were very professional, they delighted us with excellent menus always based on fish and sashimi and what can I say.... Aperitifs, wine, beer and gin galore. The catamaran very comfortable, well maintained and always clean. We hope to be able to take another holiday with them again! Guys keep it up!! 😘
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We have known the Aeolian Islands for 20 years, live them with us!

06/21/2026

Anna M.

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IT

A week in the Aeolian Islands that went far beyond a simple holiday. An authentic experience made of crystal clear sea, breathtaking sunsets, good food and special people. A heartfelt thank you to Pasquale, an exceptional skipper, always available, empathetic and able to put everyone at ease from the first moment. His sympathy and deep knowledge of the Aeolian Islands allowed us to experience the islands in the truest way, discovering enchanting bays, hidden corners and local traditions. Life on the boat made everything even more magical: sharing this adventure with people met on board, who in a few days became travel and laughter companions, was one of the most beautiful aspects of the experience. I return home with my heart full of memories, emotions and new friendships. A trip that I recommend to anyone at least once in their life and that, without a doubt, I will repeat. The Aeolian Islands seen from the sea have something special that remains inside. 💙

The wild south from Cagliari to CarloForte

06/21/2026

Danila G.

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SM

My experience has not ended, but only begun! GianRoberto, a compound name, a lot of stuff already, is a skipper with whom it is easy to share life stories and first of all a competent and sensible navigation. Sardinia is the backdrop without problems, beautiful even where it does not seem, but which explodes with poignant beauty if discovered with the eyes of those who have been able to choose "a little of the best and a little more" for the available days. Thank you very much for Gian's exquisite hospitality and the management of the whole experience made even more comfortable by Skyfall, an elegant and refined boat.
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The wild south from Cagliari to CarloForte

06/21/2026

Dario V.

-

IT

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