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Monohull yacht sailing holidays & tours in Italy

Discover more than 451 opportunities to get on board a Monohull adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

451

experiences

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4.9

4 days as free as the wind, between Capraia and Corsica

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€300

Per person

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5.0

APRIL 25TH LONG WEEKEND - PROCIDA-ISCHIA AND VENTOTENE

Duration:

4 days - 3 nights

Italy:

Gulf of Naples

Give this experience a try!

€380

Per person

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4.7

Get rid! 25 April on a sailing boat Procida, Ischia and Ventotene

Duration:

3 days - 3 nights

Italy:

Gulf of Naples

Give this experience a try!

€320

Per person

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5.0

Ponza Palmarola and Ventotene by sailboat

Duration:

6 days - 5 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€580

Per person

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4.5

Weekend di vela e Trekking all'Isola d'Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+2 travellers

have booked

€280

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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5.0

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+38 travellers

have booked

Starting from

€99

Per person

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4.5

SAIL ACADEMY - Varazze

Duration:

2 days - 1 night

Italy:

Liguria

Give this experience a try!

Starting from

€230

Per person

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5.0

Veleggiata verso il farò di Cecina con Aperitivo a bordo

Duration:

1 day - 0 nights

Italy:

Tuscany

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+2 travellers

have booked

€55

Per person

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Magic charter Sorrento Capri Amalfi Positano

Duration:

4 days - 3 nights

Italy:

Amalfi Coast

Give this experience a try!

€750

Per person

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5.0

Venice and the Venetian Lagoon

Duration:

2 days - 2 nights

Italy:

Venice and the Gulf of Trieste

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+4 travellers

have booked

€188

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!

Starting from

€433

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

10007 reviews

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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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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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