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Yacht sailing holidays & skippered tours in Italy

Discover more than 190 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

190

experiences

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5.0

Cruise to the Maddalena Archipelago and South Corsica

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+4 travellers

have booked

Starting from

€667

€785

Per person

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5.0

Aeolian Islands on a sailing boat, an exaggerated holiday!

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+6 travellers

have booked

Starting from

€417

Per person

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4.6

Relax 7 days from Olbia Arc. Maddalena-Lavezzi-Corsica S/E-Costa Smeralda

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+7 travellers

have booked

Starting from

€750

Per person

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5.0

Sailing cruise to the Pontine Islands with embarkation from Procida

Duration:

6 days - 7 nights

Italy:

Pontine Islands

Give this experience a try!

€941

€990

Per person

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Sail to new horizons aboard a Beneteau Oceanis 411

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€665

€700

Per person

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4.7

Week of August in Palmarola, Ponza and Ventotene

Duration:

6 days - 7 nights

Italy:

Pontine Islands

Give this experience a try!

€941

€990

Per person

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5.0

Summer in the Egadi Islands

Duration:

6 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€850

Per person

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4.7

Cilento by Catamaran

Duration:

6 days - 7 nights

Italy:

Campania

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+14 travellers

have booked

Starting from

€1,040

Per person

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4.9

Overwhelmed by an unusual destiny in the blue sea of Corsica

Duration:

6 days - 7 nights

Italy:

Tuscany

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+27 travellers

have booked

Starting from

€875

Per person

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4.6

Sailing cruise for all, 4 cabins 4 bathrooms Sardinia Corsica in comfort

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+2 travellers

have booked

Starting from

€930

Per person

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4.2

The south of Sardinia from Carloforte to Cagliari following the mistral

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

€990

Per person

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4.8

Whale watching cruise with WWF researcher between Elba, Capraia and North Corsica

Duration:

6 days - 7 nights

Italy:

Tuscany

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+5 travellers

have booked

€1,029

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.

-

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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