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Monohull yacht sailing holidays & tours in Italy

Discover more than 431 opportunities to get on board a Monohull adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

431

experiences

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4.9

May Day Sailing Bridge in Capraia

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€265

Per person

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4.5

Sailing on the Island of Elba

Duration:

3 days - 4 nights

Italy:

Tuscany

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Elettra

has booked

€350

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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4.9

May 1st long weekend sailing at the Pontine!

Duration:

5 days - 5 nights

Italy:

Pontine Islands

Give this experience a try!

€405

€450

Per person

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4.9

Trekking, E-bike & Sailing Experience, 1 May adventure on Elba.

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€618

€650

Per person

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4.6

May Day Long Bridge between Tuscany and Corsica

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€380

Per person

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5.0

May Day: I love you Capraia! Only for 4 guests

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€490

Per person

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Sailing day Genoa, Camogli and San Fruttuoso

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€110

Per person

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4.8

Cruise in the Gulf of Baratti

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€216

€240

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

€450

Per person

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5.0

May 1st long weekend between sailing, islands and wineries

Duration:

5 days - 5 nights

Italy:

Gulf of Naples

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+2 travellers

have booked

€550

Per person

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4.9

Long live May Day!

Duration:

5 days - 4 nights

Italy:

Aeolian Islands

Give this experience a try!

€382

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 - Monohull yacht sailing holidays & tours in Italy

10008 reviews

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A weekend of sailing between Capraia and the island of Elba

04/24/2024

Angelo C.

-

Italy

Bellissima esperienza, bella gente con uno skipper top!
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Easter on the Island of Elba

04/22/2024

Antonios S.

-

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.

-

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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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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