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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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4.9

Weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+14 travellers

have booked

Starting from

€280

Per person

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The hidden jewels of the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+20 travellers

have booked

€475

€500

Per person

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4.3

From Cagliari to Carloforte

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

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+4 travellers

have booked

€650

Per person

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5.0

Weekend in Ogliastra, breathtaking Sardinia with skipper and hostess

Duration:

2 days - 2 nights

Italy:

Southern Sardinia

Give this experience a try!

€417

Per person

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4.5

Weekend YOGA in barca a vela

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€370

Per person

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5.0

Weekend of relaxation and fun

Duration:

2 days - 2 nights

Italy:

Liguria

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+18 travellers

have booked

€280

€295

Per person

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W.E Golfo Dei Poeti-Portovenere-Rosse-Ferale

Duration:

2 days - 2 nights

Italy:

Liguria

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+37 travellers

have booked

€190

Per person

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4.7

Two hearts and a sailboat: discovering the Phlegrean Islands

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

Give this experience a try!

Starting from

€250

Per person

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4.8

DISCOVERING THE EGADI ISLANDS on the Routes of the Florio Family

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+2 travellers

have booked

€727

€765

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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4.8

Weekend on a sailing boat in ALASSIO

Duration:

2 days - 1 night

Italy:

Liguria

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+2 travellers

have booked

€270

Per person

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5.0

Wonderful holiday sailing between Elba and Giglio

Duration:

7 days - 7 nights

Italy:

Tuscany

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+2 travellers

have booked

€850

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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