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Crewed yacht sailing holidays & tours in Italy

Discover more than 56 opportunities to get on board a Crewed adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

56

experiences

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4.8

Aeolian Islands by catamaran, professional skipper/hostess, what else?

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+16 travellers

have booked

Starting from

€800

Per person

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5.0

Northern Sardinia - Stintino and Asinara with skipper and hostess/steward

Duration:

6 days - 6 nights

Italy:

Northern Sardinia

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+34 travellers

have booked

Starting from

€835

Per person

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5.0

3 days of sailing and relaxation in the Tuscan Archipelago

Duration:

3 days - 3 nights

Italy:

Tuscany

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+10 travellers

have booked

€350

Per person

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5.0

AEOLIAN ISLANDS with hostess/cook BOAT 16.5 mt exclusive x6 people

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+21 travellers

have booked

Starting from

€898

Per person

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5.0

Sail & Climb in Trieste

Duration:

3 days - 2 nights

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

€420

Per person

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Sardinia & South Corsica cruise with Skipper & Hostess - Full Board

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+2 travellers

have booked

Starting from

€1,080

€1,200

Per person

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4.4

Week in Asinara with skipper and hostess

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€830

Per person

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5.0

Taste of the sea between Elba and Capraia Hostess/Cook on board

Duration:

5 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€795

Per person

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4.8

Magical Aeolian Islands by catamaran with Stewardess on board

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

€1,100

Per person

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4.8

Pontine Ischia and Procida

Duration:

6 days - 7 nights

Italy:

Pontine Islands

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+11 travellers

have booked

€650

Per person

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4.4

Week on the west side of Sardinia with skipper and hostess

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

€830

Per person

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4.9

Magical Aeolian Islands by catamaran with hostess on board - ONE WAY

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+5 travellers

have booked

€1,000

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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