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Yacht sailing holidays & skippered tours in Italy

Discover more than 13 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

13

experiences

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4.8

Super!

Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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67 travellers

have left

Starting from

€850

€1,308

Per person

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Experience among the Egadi Islands: a dream on a sailing boat

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€405

€450

Per person

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The colors of autumn, seen from the sea on board a sailboat

Duration:

2 days - 2 nights

Italy:

Liguria

Give this experience a try!

€360

€400

Per person

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4.8

Weekend cruise from Trieste in Slovenia

Duration:

2 days - 2 nights

Italy:

Venice and the Gulf of Trieste

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27 travellers

have left

€275

€290

Per person

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4.8

Let's sail in relaxation on Lake Garda - All Inclusive

Duration:

1 day - 0 nights

Italy:

Lake Garda

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36 travellers

have left

€150

Per person

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4.9

Super!

A day sailing between Procida and Ischia

Duration:

1 day - 0 nights

Italy:

Naples & Amalfi Coast

Give this experience a try!

€80

Per person

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5.0

Super!

A day sailing in the fantastic Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

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22 travellers

have left

€90

Per person

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4.9

Super!

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Duration:

3 days - 3 nights

Italy:

Tuscany

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8 travellers

have left

€290

Per person

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4.2

Weekend of theoretical and practical course

Duration:

2 days - 1 night

Italy:

Liguria

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2 travellers

have left

€250

Per person

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5.0

Aeolian Islands on a sailing boat, an exaggerated holiday!

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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6 travellers

have left

Starting from

€334

Per person

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4.8

Super!

The sea and sailing in autumn: two days on Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€180

Per person

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4.8

Super!

Summer of San Martino in mare

Duration:

2 days - 1 night

Italy:

Tuscany

Give this experience a try!

€185

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

12179 reviews

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Magical weekend on Giglio Island

10/20/2024

Altamir T.

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Brazil

La gita in barca all'Isola del Giglio, nell'arcipelago toscano, ha superato ogni mia aspettativa. La barca a vela Luna Sul Mare è comoda e sicura. Ho una certa esperienza con le barche a vela e appena salito a bordo ho notato la cura del Capitano Saverio D'Andrea in ogni dettaglio per garantire il benessere. Tutte le attrezzature sulla barca funzionano bene e la pulizia è rigorosa. Il tour è iniziato presso l'accogliente porto turistico di Talamone. L'ancoraggio al Giglio era nella bellissima Cala dello Smeraldo, dove ho potuto godermi il bagno in mare. Il pernottamento è stato tranquillo nel dolce dondolio delle acque protette. Nella tappa successiva il capitano ci ha portato all'Argentario, dove ho potuto godermi un altro delizioso bagno a Cala Grande, prima di ritornare a Talamone. Saverio oltre a fornire un bellissimo itinerario ha saputo integrare e armonizzare la convivenza del gruppo, che è stata sempre piacevole.
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Magical Barcolana Weekend: the most famous regatta!

10/15/2024

Antonio S.

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Italy

Scoprire la Barcolana come turista e partecipante alla gara è stata un'esperienza straordinaria. La compagnia dell'equipaggio è stata positiva. Dormire in barca non è facile, ma indispensabile per gustare l'avventura della regata al massimo.
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Fantastic BARCOLANA: Racing in safety and joy!

10/15/2024

Nguyen Bao Duy T.

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United Kingdom

Paolo was an amazing skipper. I thoroughly enjoy my time at Trieste all thanks to Paolo and the crew. Barcolana itself is a party but able to participate makes it even more memorable.
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We take part in the Barcolana: local skipper, regatta and lots of parties

10/15/2024

Danilo M.

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Italy

Mi sono divertito tantissimo. Il gruppo era ben assortito ed affiatato e sono nate delle amicizie. Flavio ha saputo farci assaporare tanto l'emozione di partecipare ad un evento così coinvolgente... quanto le delizie della cucina locale! Lo rifarò l'anno prossimo!

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