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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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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

9 departures available

June - October

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

16 departures available

June - November

Starting from

€1,125

Per person - min 2 pax

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4.7

North Sardinia and South Corsica by catamaran with flybridge

Italy: Northern Sardinia

7 days - 7 nights

6 departures available

July - September

Starting from

€1,290

€1,226

Per person

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4.8

Super!

Fabulous Egadi Islands by catamaran - Stewardess on board

Italy: Aegadian islands

6 days - 7 nights

2 departures available

August - September

Starting from

€1,100

Per person

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4.8

Super!

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

Italy: Tuscany

7 days - 7 nights

5 departures available

August - September

Starting from

€850

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

Per person

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4.9

Aeolian Islands on a catamaran, professional skipper/hostess, what else?

Italy: Aeolian Islands

6 days - 7 nights

5 departures available

June - September

Starting from

€945

Per person

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4.8

Super!

From Lipari to Palermo: magical week on a catamaran with a hostess

Italy: Aeolian Islands

7 days - 7 nights

One departure available

August

€1,450

Per person

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4.8

Super!

From Palermo to Marsala: magical week on a catamaran with hostess

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€1,450

Per person

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4.8

Super!

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

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€850

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

17 departures available

June - October

Starting from

€1,320

€1,188

Per person - min 2 pax

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4.8

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

Italy: Aeolian Islands

6 days - 7 nights

6 departures available

June - September

Starting from

€1,000

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

881 reviews

Four days among the islands of the Gulf of Naples

06/8/2026

Eleonora S.

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IT

For our first catamaran experience we chose Angelo and his [hidden] and we couldn't have made a better choice! A helpful and experienced captain, who made us discover the most beautiful bays of Procida and Ischia. Together with him, the cook Diego who satisfied all our requests with incredible kindness! We are super satisfied and hope to leave soon with them! [hidden] is beautiful and very well-kept, convenient even for those who, like us, had no experience of boat holidays!
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June 2 long weekend on a catamaran in the Cinque Terre

06/7/2026

LUCA M.

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IT

what can I say ... formally it was only 96 hours along the Ligurian Levante ... but on the sea time passes along like the waves and on board Cassiopeia navigation envelops you as gently as the wind towards the coast ... But what turned a long weekend into a special experience was a set of ingredients... a nice crew with intelligent children attracted more by the sea than by a tablet ... A comfortable and spacious catamaran ... but above all Antonio, a captain who makes the difference by pampering the crew, preparing delicious food and always sailing in total safety: absolutely recommended!
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The magic of the Egadi Islands aboard a brand new catamaran

06/2/2026

Kris D.

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BE

Amazing islands, flexible chartered, professional skipper.
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The magic of the Egadi Islands aboard a brand new catamaran

06/1/2026

Dalia C.

-

BE

Very nice skipper Alessio

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