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Crewed yacht sailing holidays & tours in Italy

Discover more than 60 opportunities to get on board a Crewed adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

60

experiences

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4.3

Elba a sea of emotions - Stewardess on board - 3Cab/3Bagni

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€329

Per person

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4.8

Weekend between Amalfi, Positano and Capri

Duration:

3 days - 2 nights

Italy:

Amalfi Coast

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+19 travellers

have booked

€450

Per person

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5.0

Weekend getaway in Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€290

Per person

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4.0

All-inclusive Sardinia & Corsica Cruise (per cabin)

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+104 travellers

have booked

Starting from

€1,490

Per person

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5.0

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+4 travellers

have booked

Starting from

€1,300

€2,000

Per person

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5.0

Cruise to the Island of Elba and Capraia

Duration:

6 days - 7 nights

Italy:

Tuscany

Give this experience a try!

€1,200

Per person

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5.0

All Inclusive Cruise to the Egadi Islands

Duration:

7 days - 6 nights

Italy:

Aegadian islands

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+65 travellers

have booked

Starting from

€1,064

€1,120

Per person

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Sardinia and Costa Smeralda in Comfort - with Hostess - All Inclusive

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

Starting from

€1,690

Per person

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4.9

The Maddalena Archipelago by sail.

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+33 travellers

have booked

Starting from

€650

Per person

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4.8

ONE WAY Aeolian Islands by catamaran with hostess - from Palermo to Lipari

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+2 travellers

have booked

€1,000

Per person

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5.0

Exclusive itinerant route: Catania - Taormina - Tropea - Aeolian Islands

Duration:

8 days - 8 nights

Italy:

Sicily

Give this experience a try!

€799

Per person

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4.8

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

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+37 travellers

have booked

Starting from

€799

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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