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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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Elba and North Corsica aboard a Lagoon catamaran

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,450

Per person

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4.4

Catamaran cruise along the Cilento Coast

Italy: Campania

7 days - 7 nights

4 departures available

June - August

Starting from

€1,150

Per person

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4.4

Stellar Aegadian Islands aboard a catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€1,550

Per person

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New

Week-end a Vela in Liguria

Italy: Liguria

3 days - 2 nights

8 departures available

July - October

Starting from

€238

Per person

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3.9

6 days in Costa Smeralda and Northern Sardinia

Italy: Northern Sardinia

5 days - 5 nights

5 departures available

June - August

Starting from

€1,100

€990

Per person

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Aeolian Islands by sailboat: 6 days between volcanoes and clear waters

Italy: Aeolian Islands

6 days - 6 nights

One departure available

August

€6,950

Per person

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4.4

Premium

SARDINIA Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Northern Sardinia

6 days - 7 nights

13 departures available

June - October

Starting from

€1,445

€1,301

Per person - min 2 pax

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Sun, sea and relaxation... in the Maddalena archipelago

Italy: Northern Sardinia

6 days - 7 nights

One departure available

July

€1,390

Per person

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5.0

Capri, Sorrento, Positano and Amalfi by Catamaran

Italy: Naples & Amalfi Coast

5 days - 4 nights

One departure available

September

€645

€581

Per person

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4.8

One Way by Catamaran: From Procida to the Aeolian Islands with Style

Italy: Aeolian Islands

6 days - 7 nights

One departure available

June

€1,100

€950

Per person

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4.8

Northern Sardinia and Corsica in a comfortable Catamaran

Italy: Northern Sardinia

7 days - 7 nights

One departure available

August

€1,850

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

879 reviews

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The magic of the Egadi Islands aboard a brand new catamaran

06/2/2026

Kris D.

-

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.

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BE

Very nice skipper Alessio

The magic of the Egadi Islands aboard a brand new catamaran

05/31/2026

Johan B.

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BE

Top 👌 Top 👌 Top 👌
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CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

05/17/2026

Cristina Anna R.

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IT

Beautiful experience! Unfortunately we could not do everything planned because of the sea but it was still a wonderful holiday! Skipper Gian Marco and cook Giacinto always available and kind! We chose the "superior" cabin and had a great time! Very cozy catamaran!

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