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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.

27

experiences

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4.8

Super!

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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19 travellers

Starting from

€975

€1,500

Per person

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Maddalena and South Corsica aboard a Catamaran with Hostess

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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8 travellers

€1,512

€1,890

Per person

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4.8

Super!

Large Luxury Catamaran with Hostess - Discovering the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

€1,251

€1,390

Per person

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Summer 2025 - Catamaran week in the Pontine Islands

Duration:

7 days - 7 nights

Italy:

Pontine Islands

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14 travellers

Starting from

€1,170

€1,300

Per person

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4.8

Super!

EASTER LONG WEEKENDS - APRIL 25 - MAY 1 - LUXURY CATAMARAN IN THE AEOLIAN ISLANDS

Duration:

4 days - 4 nights

Italy:

Aeolian Islands

Give this experience a try!

€621

€690

Per person

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4.8

Super!

Aeolian Islands - Large and new catamaran equipped with every comfort

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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2 travellers

Starting from

€972

€1,080

Per person

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4.5

North Sardinia and South Corsica by catamaran with flybridge

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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110 travellers

Starting from

€846

€940

Per person

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Capri and the Amalfi Coast

Duration:

6 days - 7 nights

Italy:

Naples & Amalfi Coast

Give this experience a try!

€1,620

€1,800

Per person

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Capri, Sorrento, Positano and Amalfi by Catamaran

Duration:

5 days - 4 nights

Italy:

Naples & Amalfi Coast

Give this experience a try!

€675

€750

Per person

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4.5

The most beautiful corners of Sardinia on a Catamaran

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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8 travellers

Starting from

€950

€1,000

Per person

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4.6

Premium

All-inclusive Sardinia & Corsica Cruise (per cabin)

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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254 travellers

Starting from

€1,007

€1,060

Per person

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5.0

Tour of Elba and Capraia on a Catamaran

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

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

640 reviews

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Spring long weekends on a catamaran in the Cinque Terre

04/22/2025

Silvia D.

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Italy

Antonio e sua moglie Nadia sono stati fantastici: simpatici, organizzati e molto accoglienti, oltre ad essere esperti naviganti. La barca è pulita e ordinata, tenuta con cura. Gli spazi interni ed esterni sono davvero confortevoli. Nonostante il tempo, siamo riusciti a sfruttare al meglio i momenti di bel tempo. È stata una vacanza meravigliosa, da rifare! Grazie Antonio e Nadia 😉 A presto. Silvia e Riccardo
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Aeolian Islands by catamaran, professional skipper/hostess, what else?

10/6/2024

Marco G.

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Italy

Esperienza splendida! Prima volta per noi in barca - ma sicuramente non l’ultima! Super consigliata per chi vuole godersi il mare da una prospettiva diversa e con un ritmo più naturale. Andrea skipper super disponibile e di compagnia; Arianna super attenta e premurosa.
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Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

10/3/2024

Giovanni L.

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Switzerland

Lo skipper Maurizio ha veramente fatto del suo meglio tenendo conto del tempo atmosferico a volte inclemente che non ci ha permesso di raggiungere tutte le mete. Un saluto particolare a Tina che è una santa donna e ha tenuto insieme con allegria e simpatia un gruppo di persone di estrazione molto diversa che si sono incontrate la prima volta sul catamarano.
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Aeolian Islands on beautiful Catamaran Lagoon 421 fullopt

09/28/2024

Massimiliano C.

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Italy

Bellissima esperienza. Posti molto belli e suggestivi. Lo skipper Jack e il suo aiutante Cris sono una garanzia: competenti e capaci, hanno sempre trasmesso a tutti la sensazione che fossimo sempre in buone mani. Malgrado il tempo e i venti a volte ci fossero un po' avversi, hanno sempre trovato il modo di farci stare in sicurezza e farci godere la vacanza al 100%. Con loro e con il resto degli ospiti si è creata una bellissima atmosfera mista tra divertimento e relax. Non posso che consigliare questo team eccezionale. Grazie di cuore per questa meravigliosa esperienza! Massi

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