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Yacht sailing holidays & skippered tours in Italy

Discover more than 188 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

188

experiences

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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

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Dream Aeolian Islands

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Starting from

€891

€990

Per person

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5.0

Blue Weeks in Southern Sardinia

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

€850

Per person

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4.5

Sailing holiday with maximum comfort

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+6 travellers

have booked

Starting from

€560

Per person

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5.0

Enjoy: in the blue painted blue of the Aeolian Islands

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+6 travellers

have booked

€790

Per person

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5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+6 travellers

have booked

Starting from

€660

Per person

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Eolie a vela con skipper ed hostess, all inclusive con cucina vegana

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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Pietro

has booked

€1,750

Per person

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Aeolian Islands on a sailing boat: good food between sailing and sea!

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+9 travellers

have booked

Starting from

€990

€1,100

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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+12 travellers

have booked

€969

€1,020

Per person

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4.8

Egadi Islands - Sea, sun, relax on a brand new catamaran 2024

Duration:

6 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€1,050

Per person

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4.0

Exclusive cruise on the new Lagoon 42 of 2024

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+7 travellers

have booked

Starting from

€775

Per person

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4.0

Sailing, Relaxation and Fun in the Pontine and Phlegraean Islands on a 15-meter Boat

Duration:

7 days - 7 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€800

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.

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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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