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Yacht sailing holidays & skippered tours in Italy

Discover more than 68 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

68

experiences

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4.6

April 25 between the Tuscan islands and North Corsica.

Duration:

4 days - 4 nights

Italy:

Tuscany

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Riccardo

has booked

€350

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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4.5

Sailing day Maddalena Archipelago

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€125

Per person

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4.9

Sailing & adventure among the Egadi Islands

Duration:

4 days - 4 nights

Italy:

Aegadian islands

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+2 travellers

have booked

€500

Per person

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4.6

Long weekend of April 25 Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€345

Per person

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4.8

Long weekend on board a brand new catamaran with hostess/chef in the Egadi Islands

Duration:

4 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€590

Per person

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4.3

Wellness Cruise: Sailing and Yoga in Nature

Duration:

4 days - 5 nights

Italy:

Southern Sardinia

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+3 travellers

have booked

€600

Per person

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Long weekend 25 April

Duration:

4 days - 4 nights

Italy:

Pontine Islands

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+7 travellers

have booked

€550

Per person

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5.0

April 25th long weekend between Elba and Corsica

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€450

Per person

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4.8

LONG WEEKEND 25 April barefoot: 4 days between Capraia and the island of Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

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+4 travellers

have booked

€349

Per person

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4.2

Ponte del 25 Aprile in navigazione con rotta per la Capraia.

Duration:

4 days - 4 nights

Italy:

Tuscany

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+4 travellers

have booked

€435

Per person

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5.0

Long weekend in Capraia and North Corsica

Duration:

4 days - 4 nights

Italy:

Tuscany

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+7 travellers

have booked

€375

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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