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Yacht sailing holidays & skippered tours in Italy

Discover more than 32 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

32

experiences

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5.0

Ponza Palmarola and Ventotene by sailboat

Duration:

6 days - 5 nights

Italy:

Pontine Islands

Give this experience a try!

€580

Per person

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Gulf of Poets, Portovenere, Palmaria and the island of Tino a Vela

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€120

Per person

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4.4

Sailing Excursion Alghero ( Skipper + Hostess )

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€90

Per person

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4.9

Sailing excursion to Capri / Positano

Duration:

1 day - 0 nights

Italy:

Gulf of Naples

Give this experience a try!

€160

Per person

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4.5

Weekend di vela e Trekking all'Isola d'Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+2 travellers

have booked

€280

Per person

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5.0

Sailing, early sun and aperitif at sunset ... What else?

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+6 travellers

have booked

€59

Per person

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5.0

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+40 travellers

have booked

€99

Per person

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4.5

SAIL ACADEMY - Varazze

Duration:

2 days - 1 night

Italy:

Liguria

Give this experience a try!

€250

Per person

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5.0

A day sailing in the fantastic Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

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+4 travellers

have booked

€99

Per person

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5.0

Veleggiata verso il farò di Cecina con Aperitivo a bordo

Duration:

1 day - 0 nights

Italy:

Tuscany

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+2 travellers

have booked

€55

Per person

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Magic charter Sorrento Capri Amalfi Positano

Duration:

4 days - 3 nights

Italy:

Amalfi Coast

Give this experience a try!

€750

Per person

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5.0

Venice and the Venetian Lagoon

Duration:

2 days - 2 nights

Italy:

Venice and the Gulf of Trieste

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+4 travellers

have booked

€188

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

10894 reviews

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A weekend of sailing between Capraia and the island of Elba

04/24/2024

Angelo C.

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Italy

Bellissima esperienza, bella gente con uno skipper top!
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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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