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Yacht sailing holidays & skippered tours in Italy

Discover more than 210 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

210

experiences

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5.0

Wonderful holiday sailing between Elba and Giglio

Duration:

7 days - 7 nights

Italy:

Tuscany

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+2 travellers

have booked

Starting from

€900

Per person

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5.0

A dream adventure in the Tuscan Archipelago

Duration:

6 days - 6 nights

Italy:

Tuscany

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+3 travellers

have booked

Starting from

€711

€790

Per person

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4.9

Sailing & Adventure in the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+22 travellers

have booked

€713

€750

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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+8 travellers

have booked

Starting from

€1,035

€1,150

Per person

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Sardinia and Costa Smeralda in Comfort - with Hostess - All Inclusive

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€1,980

Per person

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5.0

Holidays in the Egadi Islands

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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+6 travellers

have booked

Starting from

€705

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

€1,093

€1,150

Per person

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Magical Aeolian Islands with chef on board a 16-meter hanse

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+5 travellers

have booked

€780

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

€740

Per person

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Sailing to discover the Egadi Islands

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+12 travellers

have booked

Starting from

€617

€686

Per person

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5.0

Magical week at the Egadi Islands in a new catamaran with hostess

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+27 travellers

have booked

Starting from

€1,200

Per person

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Aeolian Week

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

Give this experience a try!

€750

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

10891 reviews

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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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Moorings and manoeuvres course - Night Navigation and Signals - Anchorages

04/10/2024

Stefano P.

-

Italy

Corso vela, efficace, utilissimo, sintetico essenziale in una parola strepitoso. Skipper istruttore preparato, simpatico ed all'altezza del ruolo.
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A weekend of sailing between Capraia and the island of Elba

03/20/2024

davide C.

-

Italy

Enrico è un comandante che sa mettervi a proprio agio in un equilibrio di libertà e professionalità . Se vi piace oltre al vento il buon cibo siete sulla barca giusta ..

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