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Holidays, Cruises, and Catamaran Trips in Italy

The unique experience of sailing on a catamaran, with its spacious layout and exceptional comfort, combined with the chance to explore Italian coasts accessible only by sea and share moments with new friends, makes every holiday unforgettable. Treat yourself to a vacation where you wake up in a bay and enjoy breakfast surrounded by the beauty of the sea.

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New

Lunch on a catamaran overlooking the Gulf of Poets

Italy: Liguria

1 day - 0 nights

18 departures available

November

€75

Per person

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4.4

Premium

SARDINIA Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Northern Sardinia

6 days - 7 nights

23 departures available

May - October

Starting from

€1,525

€1,373

Per person - min 2 pax

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5.0

Tour of Elba and Capraia on a Catamaran

Italy: Tuscany

7 days - 6 nights

6 departures available

June - August

Starting from

€1,132

Per person

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4.8

New Year's Eve in the Gulf of Naples

Italy: Naples & Amalfi Coast

5 days - 4 nights

One departure available

December - January

€570

Per person

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4.8

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€962

€866

Per person

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New

Premium

All inclusive sailing cruise on Lagoon42 Catamaran in Sardinia with hostess

Italy: Northern Sardinia

7 days - 7 nights

11 departures available

June - October

Starting from

€2,200

Per person

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4.8

Positano, Amalfi and Capri by Catamaran

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

June - July

Starting from

€1,150

€1,035

Per person

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4.4

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

25 departures available

May - October

Starting from

€1,495

€1,346

Per person - min 2 pax

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4.3

Catamaran cruise along the Cilento Coast

Italy: Campania

7 days - 7 nights

One departure available

June - July

€1,150

Per person

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3.6

Cruise to the Egadi Islands by catamaran

Italy: Aegadian islands

6 days - 7 nights

One departure available

May - June

€1,050

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

31 departures available

April - November

Starting from

€1,820

€1,729

Per person - min 2 pax

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4.9

Egadi Islands by catamaran

Italy: Aegadian islands

7 days - 7 nights

15 departures available

June - September

Starting from

€1,100

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 - Holidays, Cruises, and Catamaran Trips in Italy

1068 reviews

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Aeolian Islands in a big and new catamaran: sea, sun, relaxation

10/4/2026

Loredana T.

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IT

A simply wonderful week, made even more special by the skipper who accompanied us and his beautiful catamaran. Maurizio is a very kind, respectful person, he is very helpful. He was able to create a beautiful balance between professionalism and conviviality, making us always feel at ease and allowing us to experience the sea with lightness and serenity. I couldn't have had a better skipper. Thank you for this wonderful week ❤️⛵️
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Aeolian Islands on a catamaran, professional skipper/hostess, what else?

10/1/2026

Federica P.

A fantastic week!!
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Weekend catamaran in Portovenere and Cinque Terre

09/29/2026

Coretta P.

-

IT

Antonio proved to be a very knowledgeable, organized, helpful and patient owner/skipper. The catamaran was found to be particularly comfortable and well maintained. Splendid itinerary and the weather also favored us. In short, a beautiful weekend!

Cous Cous Festival tra le Egadi e San Vito Lo Capo in Catamarano

09/29/2026

Sergio V.

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IT

Alessandro is first of all a great person, then as far as the week is concerned he proved to be available and attentive to the requests and desires of the crew, precious for suggestions and advice on what to do. He always accompanied us even on the ground. Helena, passionate about her work, has always prepared different dishes that are satisfying for the taste and for the eyes. It couldn't have been better than this!

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