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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

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

September - October

€950

Per person

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4.8

Super!

Capri and Amalfi Coast by catamaran - ALL INCLUSIVE

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September - October

Starting from

€1,800

Per person

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4.9

Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€1,450

€943

Per person

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4.9

Aeolian Islands - Large and new catamaran equipped with every comfort

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€1,030

€927

Per person

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4.9

Catamaran cruise to discover Amalfi, Capri, Positano, Ischia

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

October

€1,480

€1,332

Per person

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Day Cruise- Tour Golfo Dei Poeti

Italy: Liguria

1 day - 0 nights

51 departures available

September - December

€86

Per person

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4.3

Premium

Capri Dream Premium - Catamaran cruise full board

Italy: Naples & Amalfi Coast

6 days - 7 nights

One departure available

October

Starting from

€1,260

Per person - min 2 pax

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4.5

Magical Egadi Islands from Palermo

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€1,150

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

4 departures available

October - November

Starting from

€1,455

€1,382

Per person

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Week-end a Vela in Liguria

Italy: Liguria

3 days - 2 nights

14 departures available

September - December

€250

Per person

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5.0

Capri, Sorrento, Positano and Amalfi by Catamaran

Italy: Naples & Amalfi Coast

5 days - 4 nights

2 departures available

September

Starting from

€650

€585

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 - Holidays, Cruises, and Catamaran Trips in Italy

806 reviews

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Magnificent week on catamaran between Corsica and Capraia with Hostess

09/15/2025

Gaia T.

-

Italy

I give two stars respectively to hostess Manuela and travel companions. For the rest, the nervousness and unjustified anxiety of the commander led to a very unpleasant situation. A lot.
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Magnificent week on catamaran between Corsica and Capraia with Hostess

09/15/2025

Larisa N.

-

Italy

Really pleasant holiday in Corsica, with lovely places, and great company and delicious food, however the experience was ruined by the very rude captain who on one occasion left part of the passengers on an island and picked them up after 30 minutes. He was evidently very stressed about the seasonal workload he should have avoided taking this group
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Magnificent week on catamaran between Corsica and Capraia with Hostess

09/14/2025

Anna Maria C.

-

Italy

Overall positive experience.
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Aeolian Islands by catamaran, professional skipper/hostess, what else?

09/14/2025

Alessandro M.

-

Italy

This is not a review but an invitation to participate in this fantastic adventure. Fabrizio is an incredible person and skipper, he knows every rock, anchorage and current of the Aeolian Islands and then cooks divinely. Arianna will pamper you, keeping the boat always clean and tidy. you will only have to think about which costume to wear! If you are lucky, like me, to find wonderful travel companions, it will be an unforgettable experience. 5 hearts, not stars!

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