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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.

34

experiences

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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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9 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

€1,080

€1,200

Per person

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From La Maddalena to the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

€1,440

€1,600

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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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!

€477

€530

Per person

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Aeolian Slab in La Maddalena

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€810

€900

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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12 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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256 travellers

Starting from

€1,026

€1,080

Per person

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Yoga Retreat on a Catamaran

Duration:

6 days - 6 nights

Italy:

Naples & Amalfi Coast

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2 travellers

€1,950

Per person

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5.0

Tour of Elba and Capraia on a Catamaran

Duration:

7 days - 6 nights

Italy:

Tuscany

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Rosario C.

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

642 reviews

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ELBA ISLAND - Weekend in Catamaran Lagoon 42 - Departure from Piombino

05/6/2025

Debora C.

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Italy

Bellissimo catamarano molto confortevole
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Spring long weekends on a catamaran in the Cinque Terre

04/30/2025

Franca G.

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Italy

…Antonio riesce a farti uscire dalla tua quotidianità, con la sua “Kassiopea Nana” che sa cullarti fra le onde di qualsiasi mare… Partita con un’amica, ho passato 3 giorni splendidi nel mare ligure…, ho visto luoghi meravigliosi grazie anche al fatto di aver potuto fare escursioni e tappe accompagnate da ogni genere di spiegazione (grazie Nadia). Sono stata davvero bene, mi sono sentita viziata e sono riuscita a ritrovare la mia dimensione grazie a tramonti, cibo ottimo, risate e skipper speciale! Ho aperto ufficialmente la mia stagione estiva facendo il mio primo bagno in mare del 2025 !!! Grazie di cuore Antonio, per questo piccolo viaggio che serberò nel mio cuore. Sono sicura che ci rivedremo ! A presto! PS…avevi ragione… il catamarano è un altro mondo 👍!!! Carolin &Franca
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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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