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Yacht sailing holidays & skippered tours in Italy

Discover more than 172 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

172

experiences

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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

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+38 travellers

have booked

Starting from

€129

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

Between sunsets and aperitifs on a sailing boat

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€583

Per person

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5.0

Long weekend on the Island of Elba with friends

Duration:

3 days - 3 nights

Italy:

Tuscany

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+23 travellers

have booked

€371

€390

Per person

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4.3

Seven days on a sailing boat (14 meters) between Pontine and Flegree

Duration:

7 days - 6 nights

Italy:

Pontine Islands

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+6 travellers

have booked

€790

Per person

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4.3

Crociera 7 gg su maxi yacht vela 22 mt con skipper pontine e flegree

Duration:

7 days - 6 nights

Italy:

Pontine Islands

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+24 travellers

have booked

€1,390

Per person

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4.9

Weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+2 travellers

have booked

€437

Per person

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4.5

Weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€420

Per person

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5.0

Relaxing weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+15 travellers

have booked

€475

Per person

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5.0

Weekend at the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+2 travellers

have booked

€525

Per person

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4.9

Sailboat Trip and Aperitif in the Gulf of Tigullio - All inclusive!

Duration:

1 day - 0 nights

Italy:

Liguria

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+52 travellers

have booked

€90

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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