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Yacht sailing holidays & skippered tours in Italy

Discover more than 187 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

187

experiences

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4.9

Adventure Flotilla in Costa Smeralda and Corsica

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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+3 travellers

have booked

€799

€999

Per person

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4.9

Beautiful bays between North Sardinia and South Corsica on a catamaran

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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+15 travellers

have booked

Starting from

€945

€1,050

Per person

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4.2

La Maddalena and its archipelago up to the south of Corsica.

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

Starting from

€600

Per person

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5.0

Tour of Elba and Capraia

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€1,300

Per person

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4.9

Sun & Sea Sailing in the Tuscan Archipelago

Duration:

7 days - 7 nights

Italy:

Tuscany

Give this experience a try!

€836

€880

Per person

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5.0

Sailing, swimming and aperitif at sunset ... What else?

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+4 travellers

have booked

Starting from

€79

Per person

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5.0

Gulf of Naples, Pontine, Amalfi Coast... Sailing in comfort!

Duration:

7 days - 7 nights

Italy:

Gulf of Naples

Give this experience a try!

€1,490

Per person

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4.7

Discovering the most beautiful corners of Sardinia

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+2 travellers

have booked

Starting from

€998

€1,050

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+21 travellers

have booked

Starting from

€740

Per person

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Aeolian Week

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

Give this experience a try!

€750

Per person

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Dream Aeolian Islands

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€891

€990

Per person

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4.5

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Duration:

6 days - 7 nights

Italy:

Pontine Islands

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+9 travellers

have booked

Starting from

€664

€699

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 - Yacht sailing holidays & skippered tours in Italy

10893 reviews

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Easter on the Island of Elba

04/22/2024

Antonios S.

-

Italy

Anche se il tempo non ha aiutato, è stata una bellissima esperienza
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Trekking and sailing weekend on the island of Elba

04/22/2024

Sara C.

-

Italy

Bellissima esperienza,grazie alla cordialità e professionalità di Marco e i compagni di avventura. Ho apprezzato molto anche la possibilità di fare trekking. Consigliatissimo!!
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Luxury sailing in the Gulf of Poets

04/15/2024

Antonio C.

-

Italy

Giornata splendida, mare e barca perfetti, altissimo valore aggiunto l’equipaggio, simpatico gentile preparato ma soprattutto disponibile, e Costanza ottima cuoca, esperienza fantastica, da ripetere!!
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Veleggiata verso il farò di Cecina con Aperitivo a bordo

04/11/2024

maurizio r.

-

Italy

Grazie per la bella domenica di relax in barca Maurizio e Giuliana

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