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Yacht sailing holidays & skippered tours in Italy

Discover more than 122 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

122

experiences

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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

€561

€590

Per person

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4.7

Cilento by Catamaran

Duration:

6 days - 7 nights

Italy:

Campania

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+10 travellers

have booked

€1,040

Per person

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4.6

Sicily on a Sailing Boat in the Egadi Islands

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+4 travellers

have booked

Starting from

€599

Per person

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4.8

The Egadi Islands as you've never seen them before on a 16-meter boat with hostess

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+37 travellers

have booked

€900

Per person

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4.9

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+46 travellers

have booked

Starting from

€730

Per person

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4.9

Sailing to discover north-western Sicily

Duration:

6 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

€1,000

Per person

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Tour in the marine protected area of Tavolara and Cala Moresca

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€70

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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+11 travellers

have booked

Starting from

€561

€590

Per person

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4.5

Egadi, a paradise for sailing and snorkelling

Duration:

7 days - 8 nights

Italy:

Aegadian islands

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+38 travellers

have booked

Starting from

€600

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

Give this experience a try!

€630

Per person

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4.9

Day on Lake Maggiore

Duration:

1 day - 0 nights

Italy:

Lake Maggiore

Give this experience a try!

€130

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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