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Yacht sailing holidays & skippered tours in Italy

Discover more than 188 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

188

experiences

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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!

€720

Per person

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Your Aeolian Islands

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+11 travellers

have booked

€903

€950

Per person

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4.5

North Sardinia at full speed!

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

Starting from

€800

Per person

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5.0

All inclusive day trip sailing around the Golfo Paradiso - flex dates

Duration:

1 day - 0 nights

Italy:

Liguria

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+12 travellers

have booked

€130

€144

Per person

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4.5

The Aeolian Islands as you've never seen them before!

Duration:

8 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

€850

Per person

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4.9

Gulf of Tigullio on a Sailboat - All inclusive!

Duration:

1 day - 0 nights

Italy:

Liguria

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+152 travellers

have booked

€149

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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+8 travellers

have booked

€780

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

Starting from

€270

Per person

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5.0

A dream adventure in the Tuscan Archipelago

Duration:

6 days - 6 nights

Italy:

Tuscany

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+3 travellers

have booked

Starting from

€756

€840

Per person

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4.9

Sailing & Adventure in the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+34 travellers

have booked

Starting from

€713

€750

Per person

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4.9

Adventure Flotilla in Costa Smeralda and Corsica

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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+3 travellers

have booked

€799

€999

Per person

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4.9

Beautiful bays between North Sardinia and South Corsica on a catamaran

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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+19 travellers

have booked

Starting from

€945

€1,050

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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