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Crewed yacht sailing holidays & tours in Italy

Discover more than 49 opportunities to get on board a Crewed adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

49

experiences

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5.0

Overwhelmed by an unusual destiny in the blue sea of Corsica

Duration:

6 days - 7 nights

Italy:

Tuscany

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+6 travellers

have booked

Starting from

€662

Per person

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4.4

Sailing between the islands of North Sardinia and South Corsica with Skipper and Hostess

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+14 travellers

have booked

Starting from

€900

Per person

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4.3

July, how good I want you! - Stewardess on board - 3 Cab/ 3 Bathrooms

Duration:

4 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€429

Per person

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4.8

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

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+10 travellers

have booked

Starting from

€865

€910

Per person

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4.5

Classic is a chic ! Sailing between La Maddalena and Northern Sardinia

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€1,400

Per person

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5.0

Cruise to La Maddalena and Costa Smeralda

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€1,200

Per person

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4.9

Magical week at the Egadi Islands on a new catamaran

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+28 travellers

have booked

Starting from

€1,200

Per person

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5.0

Wonderful week on a catamaran between Elba, Corsica and Capraia

Duration:

6 days - 7 nights

Italy:

Tuscany

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+43 travellers

have booked

Starting from

€1,250

Per person

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4.3

Elba, all the colors of the big blue - Stewardess on board - 3 Cab/ 3 Bathrooms

Duration:

5 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€770

Per person

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4.8

Lampedusa, Linosa and Lampione, islands on the high seas - all inclusive

Duration:

6 days - 7 nights

Italy:

Pantelleria and Lampedusa

Give this experience a try!

Starting from

€760

€800

Per person

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5.0

Cruise in the beautiful northern Sardinia (around Tavolara)

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€1,200

Per person

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4.6

Premium

Italy Experience - 8 giorni in catamarano ALL INCLUSIVE con hostess

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Starting from

€2,890

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

547 reviews

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Take part in the 55th Barcolana with everything included

10/11/2023

Peter C.

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Italy

Fantastica esperienza! Nonostante il vento quasi inesistente Alberto e Federica ci hanno fatto sentire tutta l'energia della Barcolana! Grazie!
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Weekend on the Island of Elba...Hostess on board

10/9/2023

Barbara B.

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Italy

la professionalità e la compagnia di Vittorio e Giulia ci hanno regalato un week end bellissimo. Affidabili, super disponibili e divertenti Consigliatissimo!!!
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All inclusive weekend in the Gulf of Alassio

10/6/2023

John C.

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Italy

Sarà stata la sfortuna o l’improvvisazione ma non abbiamo navigato con Daniele e nonostante l’impegno di Carmen il we “non ha girato” (barca bloccata in porto da “problemi burocratici”) Mi spiace ma non riproverò
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From the Egadi Islands to the Cous Cous Fest of San Vito Lo Capo on a 16-metre boat (private bathroom) with Hostess

10/6/2023

genevieve s.

-

Australia

Amazing trip with the best crew! Highly recommended.

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