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Yacht sailing holidays & skippered tours in Italy

Discover more than 209 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

209

experiences

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4.8

Whale watching cruise with WWF researcher between the Tuscan Archipelago and Northern Corsica

Duration:

6 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€919

Per person

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South Sardinia

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

€874

€920

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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4.8

Sail & Tour: Sorrento, Capri, Positano, Amalfi - with 2 nights in villa

Duration:

5 days - 4 nights

Italy:

Amalfi Coast

Give this experience a try!

€995

Per person

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4.5

The Aeolian Islands as you've never seen them before

Duration:

4 days - 3 nights

Italy:

Aeolian Islands

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+4 travellers

have booked

Starting from

€450

Per person

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4.8

Little sailors grow up: 5 days sailing on the island of Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

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+3 travellers

have booked

€490

Per person

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The secrets of the Aeolian Islands

Duration:

5 days - 5 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€700

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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5.0

Elba, Corsica and Capraia sailing

Duration:

6 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€740

Per person

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The Aeolian Islands in an exclusive boat

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+2 travellers

have booked

Starting from

€800

Per person

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4.8

All in the Family: 5 days sailing on Elba on a comfortable 17m boat

Duration:

5 days - 4 nights

Italy:

Tuscany

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+4 travellers

have booked

€490

Per person

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5.0

Capraia & North Corsica: We love to travel a lot

Duration:

7 days - 6 nights

Italy:

Tuscany

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+20 travellers

have booked

Starting from

€820

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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