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Crewed yacht sailing holidays & tours in Italy

Discover more than 40 opportunities to get on board a Crewed adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

40

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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5.0

Magical week in the Pontine Islands (and Phlegraeans)

Duration:

7 days - 7 nights

Italy:

Pontine Islands

Give this experience a try!

€864

€960

Per person

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5.0

Magical weekend in Palmarola and Ponza

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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35 travellers

Starting from

€288

€320

Per person

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5.0

Route to the Egadi Islands: Wind, Flavors and Sea

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Duration:

6 days - 7 nights

Italy:

Tuscany

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115 travellers

Starting from

€714

€793

Per person

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4.7

The Egadi Islands as you've never seen them before on a 16-meter boat with a professional hostess

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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87 travellers

€1,332

€1,460

Per person

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4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, and Sorrento

Duration:

5 days - 5 nights

Italy:

Naples & Amalfi Coast

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10 travellers

Starting from

€1,059

€1,115

Per person

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4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Duration:

6 days - 6 nights

Italy:

Naples & Amalfi Coast

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6 travellers

€1,316

€1,385

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

Cruise between Sardinia and Corsica with hostess

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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Serena

€1,250

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 - Crewed yacht sailing holidays & tours in Italy

668 reviews

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All Inclusive Cruise to the Egadi Islands

10/8/2024

Francesca D.

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Italy

Scrivo una sola parola: speciali. Agata e Leonardo prima di tutto. Le prelibatezze a bordo. La barca. I luoghi.
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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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Mini cruise Syracuse - Marzamemi with hostess and galley included

09/30/2024

Francesco C.

-

Italy

Capitano e hostess fantastici! Una bellissima avventura immersiva nel mare e nel sole!
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Magical weekend in Palmarola and Ponza

09/29/2024

Loredana D.

-

Italy

Ottima esperienza, in barca con Federico e Costanza. Professionali nel condurre la barca e attenti a mettere a proprio agio gli ospiti. La barca è molto bella e spaziosa. Abbiamo passato tre gironi in allegria, veleggiando e in relax.

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