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Private yacht sailing holidays with skipper in Italy

Chartering a sailing boat in Italy will let you discover a new way of travelling new way of travelling in complete freedom. Choose between a catamaran or a sailing boat and embark with an experienced skipper to discover Tuscany, Sicily, Tuscany, Sicily, Sardinia and many other destinations.

421

experiences

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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

€400

Per person

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5.0

Sailing, early sun and aperitif at sunset ... What else?

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+6 travellers

have booked

€59

Per person

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4.6

April 25 between the Tuscan islands and North Corsica.

Duration:

4 days - 4 nights

Italy:

Tuscany

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Riccardo

has booked

€350

Per person

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Gulf of Poets, Portovenere, Palmaria and the island of Tino a Vela

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€120

Per person

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4.9

Sailing & adventure among the Egadi Islands

Duration:

4 days - 4 nights

Italy:

Aegadian islands

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+2 travellers

have booked

Starting from

€450

Per person

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4.6

Long weekend of April 25 Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€345

Per person

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4.8

Long weekend on board a brand new catamaran with hostess/chef in the Egadi Islands

Duration:

4 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€590

Per person

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4.3

Wellness Cruise: Sailing and Yoga in Nature

Duration:

4 days - 5 nights

Italy:

Southern Sardinia

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+3 travellers

have booked

€600

Per person

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Long weekend 25 April

Duration:

4 days - 4 nights

Italy:

Pontine Islands

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+7 travellers

have booked

€550

Per person

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5.0

April 25th long weekend between Elba and Corsica

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€450

Per person

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4.8

LONG WEEKEND 25 April barefoot: 4 days between Capraia and the island of Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

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+4 travellers

have booked

€349

Per person

Why book a holiday with Sailsquare?

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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 - Private yacht sailing holidays with skipper in Italy

112 reviews

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Easter on the Island of Elba

04/22/2024

Antonios S.

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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.

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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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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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Between aperitif sunsets and sailings on the island of Elba

09/19/2023

Lorenzo M.

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Monaco

La nostra prima vacanza in barca a vela. La barca è perfetta, spaziosa e confortevole, con due bagni separati (skipper e ospiti). Luca il proprietario ha reso l'esperienza speciale, una persona eccezionale, cuoco straordinario e padrone di casa accogliente. Navigare tra Elba, Corsica e Capraia con lui è stato un autentico piacere. è stato come essere in barca con un amico di lunga data o uno zio. Nota per i futuri naviganti: è golossissimo (come noi) di gorgonzola! Esperienza super consigliata specialmente per chi è alla prima esperienza. Purtoppo non possiamo dire altrettanto di sailsquare, ad oggi non abbiamo ancora ricevuto documenti come ricevuta di pagamento o contratto di charter. Inoltre ad una richiesta di assistenza non siamo mai stati ricontattati.

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