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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

21 departures available

May - 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

25 departures available

May - October

Starting from

€1,540

€1,463

Per person

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4.9

Super!

Isole Egadi in catamarano con hostess/cuoco a bordo

Italy: Aegadian islands

7 days - 7 nights

One departure available

June

€1,100

Per person

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4.3

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

25 departures available

May - October

Starting from

€1,320

€1,188

Per person - min 2 pax

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5.0

NEW YEAR'S EVE in the Gulf of Naples & Amalfi Coast on a catamaran with hostess

Italy: Naples & Amalfi Coast

4 days - 4 nights

One departure available

December - January

€620

Per person

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4.3

Premium

TUSCANY Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Tuscany

7 days - 7 nights

2 departures available

July - August

Starting from

€2,390

Per person - min 2 pax

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5.0

Positano, Amalfi and Carpi by Catamaran

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

June - July

€1,150

€1,035

Per person

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Day Cruise- Tour Golfo Dei Poeti

Italy: Liguria

1 day - 0 nights

8 departures available

December

€86

Per person

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Week-end a Vela in Liguria

Italy: Liguria

3 days - 2 nights

3 departures available

December

€250

Per person

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5.0

The magic of winter on the Amalfi Coast with Hostess

Italy: Naples & Amalfi Coast

4 days - 4 nights

2 departures available

January - December

€580

Per person

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4.7

North Sardinia and South Corsica by catamaran with flybridge

Italy: Northern Sardinia

7 days - 7 nights

14 departures available

May - September

Starting from

€940

€846

Per person

Why book a holiday with Sailsquare?

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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

817 reviews

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The magic of the Egadi Islands aboard a brand new catamaran

10/5/2025

Marco B.

-

Italy

A wonderful experience, sea, great company and fantastic food!
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Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

09/29/2025

Stella H.

-

France

Fantastic destination. Great sized catamaran. Food provided by our hostess was good. There are a few of issues that need highlighting: 1. The size of the boat and its starting point changed after I booked online. 2. I had asked if a single supplement applied to my booking as (at the point of booking) the boat/catamaran only had 4 berths. I was told there wasn’t a supplement. We were assigned a larger boat and I was allotted a single cabin - the same size as for the hostess/chef. 3. I did not receive a confirmation by email of what I had booked (so had no evidence of what I was to expect when I arrived). I was in a cabin suitable for a child and had to share a bathroom. There was no WiFi available. I had no exterior window. The fan in my room only worked by connecting 2 loose wires (like hotwiring a car!). The sockets in my room worked intermittently. 4. The skipper was extremely competent in his professional work. However, his English was not good enough to be listed as a second language. In addition, he could have been more regular about informing ALL the passengers at the same time about the itinerary for the day (which differed significantly in order from that on the website). Informing us whilst we were eating would have been the perfect time. 5. On the day of departure we were asked to meet 2 hours earlier than arranged but the cleaners had not finished their work and we left 2 hours behind schedule. This we were sitting around for 4 hours unnecessarily. Better communication might have avoided this. 6. The wording for the itinerary is not clear regarding the transfer from an airport. I feel it needs to be explicit that this isn’t included. 7. The skipper was in a hurry to return to port on the night before last and omitted a final swim stop. He left the boat before the others.
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Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

09/28/2025

Sara D.

-

Italy

Beyond expectations...
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Aeolian Islands - Large and new catamaran equipped with every comfort

09/28/2025

Simon F.

-

Austria

Thank you maurizio and dea for making this an amazing trip Very nice islands perfect food nice boat experience

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