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Crewed yacht sailing holidays & tours in Italy

Discover more than 25 opportunities to get on board a Crewed adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

25

experiences

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5.0

Super!

Route to the Egadi Islands: Wind, Flavors and Sea

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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2 travellers

Starting from

€585

€650

Per person

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5.0

Aeolian Islands - A week on a sailing boat with skipper and assistant

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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35 travellers

Starting from

€786

€873

Per person

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Sailing, Yoga, Trekking, Biking to discover the Etruscan coast

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€225

€250

Per person

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4.8

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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28 travellers

Starting from

€865

€910

Per person - min 2 pax

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Full board South-East Sardinia Cruise with hostess

Duration:

6 days - 6 nights

Italy:

Southern Sardinia

Give this experience a try!

€1,226

€1,290

Per person

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May 1st long weekend in catamaran Aeolian Islands with hostess

Duration:

5 days - 4 nights

Italy:

Aeolian Islands

Give this experience a try!

€532

€560

Per person

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Full board South Sardinia Cruise with hostess

Duration:

6 days - 6 nights

Italy:

Southern Sardinia

Give this experience a try!

Starting from

€1,226

€1,290

Per person

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3.0

Southern Sardinia on a beautiful 16m boat with HOSTESS

Duration:

7 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

Starting from

€1,330

€1,400

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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167 travellers

Starting from

€1,416

€1,490

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!

€1,390

Per person

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Discovering the Aeolian Islands by catamaran with hostess

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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18 travellers

Starting from

€1,250

Per person

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4.9

Easter 2025 on the French Riviera from Imperia Hostess on board.

Duration:

3 days - 3 nights

Italy:

Liguria

Give this experience a try!

€375

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

661 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.

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Italy

Capitano e hostess fantastici! Una bellissima avventura immersiva nel mare e nel sole!
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Magical summer 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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