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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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4.8

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

3 departures available

September - October

Starting from

€950

Per person

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4.8

Super!

Dream sailing on a fully-equipped catamaran

Italy: Southern Sardinia

7 days - 7 nights

2 departures available

August - September

Starting from

€850

Per person

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4.9

Aeolian Islands by catamaran, professional skipper/hostess, what else?

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€870

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 - November

Starting from

€1,455

€1,382

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

3 departures available

September - October

Starting from

€1,800

Per person

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4.8

Super!

Egadi Islands by catamaran with stewardess and cook on board

Italy: Aegadian islands

7 days - 7 nights

2 departures available

September

Starting from

€1,100

Per person

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3.8

The most beautiful corners of Sardinia on a Catamaran

Italy: Northern Sardinia

7 days - 7 nights

One departure available

August

€1,250

Per person

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4.8

Fabulous Egadi Islands by catamaran - Stewardess on board

Italy: Aegadian islands

7 days - 7 nights

One departure available

August - September

€1,300

Per person

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5.0

Capri, Sorrento, Positano and Amalfi by Catamaran

Italy: Naples & Amalfi Coast

5 days - 4 nights

4 departures available

September

Starting from

€650

€585

Per person

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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

3 departures available

August - September

Starting from

€950

€760

Per person

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3.8

3 days in Sardinia - Costa Smeralda or AMP Tavolara

Italy: Northern Sardinia

3 days - 3 nights

One departure available

September

€1,000

Per person

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4.3

Premium

Capri Dream Premium - Catamaran cruise full board

Italy: Naples & Amalfi Coast

6 days - 7 nights

3 departures available

August - October

Starting from

€1,260

Per person - min 2 pax

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

733 reviews

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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

08/21/2025

Andrea P.

-

Italy

An experience absolutely to be repeated. The organization of the trip was managed by LaFlottiglia with excellent success. It was the first group trip (I left alone) and despite the initial fear I found a magnificent group of both skippers and guys with whom I shared the experience. The established itinerary may undergo small variations due to bad weather but still very valid. If I have to find a flaw, it is due to the fact that we were not always cohesive in terms of distances to the other boats, this made it complicated to interact with the members of the other crews. For the rest, I have all had very pleasant experiences that I will definitely repeat.
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Different Flotilla: Party and new friends in the Aeolian Islands

08/19/2025

Giulia B.

-

Italy

An unforgettable experience! The organization was impeccable: the staff puts energy and passion into every detail, offering original and super fun activities. Every day was a party, with music, smiles and moments of sharing with special people, all immersed in the wonderful setting of the Aeolian Islands: crystal clear sea, breathtaking sunsets and views that will remain in the heart. The flotilla formula is truly unique, because it allows you to meet many people and create authentic bonds thanks to the many moments of common life. I started with high expectations, but reality far exceeded them. I can't wait to leave with you again!
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Different Flotilla: Party and new friends in the Aeolian Islands

08/19/2025

Giancarlo A.

-

Italy

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Different Flotilla: Party and new friends in the Aeolian Islands

08/18/2025

Marzia I.

-

Italy

Back from a week in the flotilla, my first flotilla of my life. What can I say a wonderful experience, which I will really struggle to forget. Exceptional organization, pure fun, great people, you leave with strangers who in just 6 days become friends and win your heart. As soon as you set sail, you leave your thoughts of the land, and what begins is an adventure full of emotions and sensations that you will always carry in your heart. Thanks to all the staff for giving us a dream!

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