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Courses & regatta yacht sailing holidays & tours in Italy

Discover more than 13 opportunities to get on board a Courses & regatta adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

13

experiences

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5.0

Cruise course in Sardinia

Duration:

7 days - 6 nights

Italy:

Northern Sardinia

Give this experience a try!

€648

€720

Per person

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5.0

Shores Workshop - The Aegadian Islands

Duration:

7 days - 6 nights

Italy:

Aegadian islands

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+3 travellers

have booked

€831

€875

Per person

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4.8

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€290

Per person

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5.0

Holiday and sailing school between the Tuscan archipelago and Corsica

Duration:

7 days - 6 nights

Italy:

Tuscany

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+28 travellers

have booked

€750

Per person

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Sailing cruise on the Gargano

Duration:

6 days - 7 nights

Italy:

Puglia

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+2 travellers

have booked

Starting from

€699

Per person

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5.0

Fantastic BARCOLANA: Racing in safety and joy!

Duration:

2 days - 1 night

Italy:

Venice and the Gulf of Trieste

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+3 travellers

have booked

€249

Per person

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4.7

Magical Weekend of the Barcolana: the most famous regatta!

Duration:

3 days - 3 nights

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

Starting from

€380

Per person

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4.8

Super!

We take part in the Barcolana: local skipper, regatta and lots of parties

Duration:

2 days - 2 nights

Italy:

Venice and the Gulf of Trieste

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+2 travellers

have booked

€393

Per person

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5.0

Sailing in southern Sardinia

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

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+8 travellers

have booked

Starting from

€790

Per person

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4.8

Basic sailing course on cabin cruisers

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€225

Per person

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Sailing cruise course in Sardinia

Duration:

7 days - 6 nights

Italy:

Northern Sardinia

Give this experience a try!

€720

Per person

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4.8

Advanced Sailing Course on offshore cabin cruisers

Duration:

2 days - 2 nights

Italy:

Tuscany

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Giovanni

has booked

€225

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 - Courses & regatta yacht sailing holidays & tours in Italy

535 reviews

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Holiday and sailing school between the Tuscan archipelago and Corsica

07/26/2024

RITA M.

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Italy

Bellissima esperienza, consiglio vivamente anche a chi come ma è alle prime armi in questa attività che ti riconnette alla natura e al tuo io interiore, Un grazie particolare a Diego skipper competente, paziente e alla mano, specialie il suo sugo tonno e origano assolutamente da provare.Ottima la compagnia! 💚
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School-holiday cruise from Marina di Pisa to Cagliari

07/26/2024

Joel B.

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France

Amazing 10 days. Three islands Isola d Elva Corsica and Sardinia. Fulvio and Edoardo are sailing instructors. Safety and knowledge are on board. Fun and kindness also. Highly recommended. They even managed for perfect weather and good wind.
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Holiday and sailing school between the Tuscan archipelago and Corsica

07/20/2024

roberto c.

-

Italy

Consiglio Diego a tutti, sia agli appassionati di vela che ai vacanzieri.
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Sail, or learn to sail, in Castelsardo in Sardinia

07/16/2024

Anna Jessica W.

-

Italy

We haf a wonderful experience on the sail boat. We went for three hours and enjoyed a bit of swimming as well as some sailing. Sasha was very kind to answer all our questions regarding sailing. Thank you very much -we willl be back in autumn.

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