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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

8 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

9 departures available

June - November

Starting from

€1,455

€1,382

Per person

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4.9

Unforgettable Catamaran Cruise in Elba, Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

8 departures available

June - August

Starting from

€1,148

€861

Per person

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4.8

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

June - August

Starting from

€2,062

€1,340

Per person

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5.0

Super!

Tour of Elba and Capraia on a Catamaran

Italy: Tuscany

7 days - 6 nights

4 departures available

July - August

Starting from

€1,100

Per person

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4.5

North Sardinia and South Corsica by catamaran with flybridge

Italy: Northern Sardinia

7 days - 7 nights

7 departures available

June - September

Starting from

€690

Per person

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4.8

Super!

Dream sailing on a fully-equipped catamaran

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

June - July

Starting from

€940

Per person

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4.8

Fabulous Egadi Islands by catamaran - Stewardess on board

Italy: Aegadian islands

7 days - 7 nights

3 departures available

June - September

Starting from

€1,180

Per person

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4.9

Super!

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

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

August - September

Starting from

€870

Per person

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4.8

Super!

Egadi Islands by catamaran Astrea 42 of 2020 - Stewardess/Cook on board

Italy: Aegadian islands

7 days - 7 nights

2 departures available

July

Starting from

€1,200

Per person

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4.5

The most beautiful corners of Sardinia on a Catamaran

Italy: Northern Sardinia

7 days - 7 nights

8 departures available

June - September

Starting from

€1,000

€950

Per person

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5.0

Super!

Week on the Costa Smeralda on a full optional catamaran!

Italy: Northern Sardinia

6 days - 6 nights

5 departures available

June - August

Starting from

€1,100

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

648 reviews

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Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

06/14/2025

Linda H.

-

Australia

It was an amazing experience exceeded my expectations. The all female crew were excellent They went over and above their duties. They were very caring respectful and tried to make our experience a positive enjoyable experience which they did perfectly. It was one of the best Sailing trips I have ever done.
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Weekend catamaran in Portovenere and Cinque Terre

06/1/2025

Alessio C.

-

Italy

Abbiamo trascorso 3 giorni in posti meravigliosi e in buona compagnia. Lo skipper Antonio è stato super disponibile e professionale, che dire, ci si rivedrà sicuramente!
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Weekend catamaran in Portovenere and Cinque Terre

05/27/2025

Luigi S.

-

Italy

Ho trascorso un fantastico weekend in barca a vela che ha superato tutte le mie aspettative. Lo skipper è stato eccezionale: non solo era competente e professionale, ma anche comprensivo e paziente con tutti noi. Ha saputo creare un'atmosfera rilassata e piacevole, rendendo l'esperienza ancora più memorabile. La barca era pulita e ben tenuta, il che ha contribuito a farci sentire a nostro agio e sicuri durante tutta la navigazione. Ogni dettaglio era curato con attenzione, dimostrando un alto livello di manutenzione e cura. L'equipaggio era affiatato e collaborativo, creando un ambiente armonioso e divertente. È stato un piacere condividere questa avventura con persone così appassionate e disponibili. Abbiamo lavorato insieme come una vera squadra, rendendo ogni momento speciale. In sintesi, consiglio vivamente questa esperienza a chiunque desideri vivere un weekend in barca a vela indimenticabile.
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Weekend catamaran in Portovenere and Cinque Terre

05/26/2025

Valentina R.

-

Italy

È stato un vero piacere di navigare con Antonio, che si distingue per professionalità e competenza. Disponibile, attento e pieno d’iniziativa, trasmette sicurezza e affidabilità in ogni situazione. Antonio è una persona solare e accogliente, capace di far sentire ogni ospite a proprio agio. L’esperienza di bordo è piacevole, coinvolgente e sempre ben organizzata. Antonio è uno skipper preparato, con cui è stato un piacere salpare.

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