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Yacht sailing holidays & skippered tours in Italy

Discover more than 32 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

32

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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4.8

Long weekend at the Capraia Squid Festival

Duration:

4 days - 3 nights

Italy:

Tuscany

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Alessandra G.

has left

€320

€390

Per person

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5.0

Long weekend at the Capraia Squid Festival

Duration:

3 days - 3 nights

Italy:

Tuscany

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3 travellers

have left

€320

€390

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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4.5

Autumn on a Sailing Boat in the Gulf of Naples

Duration:

2 days - 2 nights

Italy:

Naples & Amalfi Coast

Give this experience a try!

€198

€220

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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4.8

Super!

Scopello, San Vito and Egadi: friends, good food sailing

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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22 travellers

have left

€523

€550

Per person

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4.6

Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!

Duration:

3 days - 2 nights

Italy:

Tuscany

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7 travellers

have left

€275

€290

Per person

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4.8

Squid Festival: let's close the season on a high note! - on board a 17mt boat

Duration:

3 days - 3 nights

Italy:

Tuscany

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4 travellers

have left

€361

Per person

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5.0

Aeolian Islands in serenity. Boat with 3 cabins and 3 bathrooms

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

€433

Per person

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4.6

Squid Festival! - Capraia Isola

Duration:

3 days - 3 nights

Italy:

Tuscany

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3 travellers

have left

€370

Per person

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5.0

Capraia under full sail / trekking on the island

Duration:

3 days - 2 nights

Italy:

Tuscany

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36 travellers

have left

€240

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 - 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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