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Yacht sailing holidays & skippered tours in Italy

Discover more than 122 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

122

experiences

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5.0

Cruise between Elba, Corsica Del Nord and Capraia with PROFESSIONAL SKIPPER AND COOK

Duration:

6 days - 7 nights

Italy:

Tuscany

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+29 travellers

have booked

€713

€750

Per person

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4.8

Whale watching cruise with WWF researcher between the Tuscan Archipelago and Northern Corsica

Duration:

6 days - 6 nights

Italy:

Tuscany

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Anna A.

has booked

Starting from

€889

Per person

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4.9

A week of sea, nature and fun in the Pontine Islands!

Duration:

6 days - 7 nights

Italy:

Pontine Islands

Give this experience a try!

€621

€690

Per person

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The secrets of the Aeolian Islands

Duration:

5 days - 5 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€750

Per person

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4.5

The Aeolian Islands as you've never seen them before

Duration:

4 days - 3 nights

Italy:

Aeolian Islands

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+4 travellers

have booked

Starting from

€380

Per person

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4.9

Weeks on a sailing boat in the Tuscan Archipelago: Elba Capraia Giglio

Duration:

7 days - 6 nights

Italy:

Tuscany

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+13 travellers

have booked

€625

Per person

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5.0

Elba, Corsica and Capraia sailing

Duration:

6 days - 6 nights

Italy:

Tuscany

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+15 travellers

have booked

€630

Per person

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5.0

Capraia & North Corsica: We love to travel a lot

Duration:

7 days - 6 nights

Italy:

Tuscany

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+30 travellers

have booked

Starting from

€700

Per person

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4.5

4-day midweek tour of the Pontine Islands

Duration:

4 days - 3 nights

Italy:

Pontine Islands

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+2 travellers

have booked

Starting from

€280

Per person

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4.9

Midweek getaway between Elba and Capraia

Duration:

3 days - 3 nights

Italy:

Tuscany

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+16 travellers

have booked

€250

Per person

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5.0

Midweek relaxing in the Pontine Mountains

Duration:

4 days - 3 nights

Italy:

Pontine Islands

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+5 travellers

have booked

Starting from

€412

Per person

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5.0

4 weekdays in the Pontine Islands

Duration:

4 days - 3 nights

Italy:

Pontine Islands

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+10 travellers

have booked

Starting from

€350

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

10894 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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