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Yacht sailing holidays & skippered tours in Italy

Discover more than 228 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

228

experiences

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Sardinia and Costa Smeralda in Comfort - with Hostess - All Inclusive

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€1,690

Per person

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4.8

Elba Capraia and Caorsica - Sea and Colour

Duration:

6 days - 7 nights

Italy:

Tuscany

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+10 travellers

have booked

Starting from

€520

Per person

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5.0

Explore Sardinia's coastline! Skipper & Hostess - All included

Duration:

6 days - 6 nights

Italy:

Northern Sardinia

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+13 travellers

have booked

€1,490

Per person

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Sailing to discover the Egadi Islands

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+12 travellers

have booked

€562

€624

Per person

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Aeolian Week

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

Give this experience a try!

€750

Per person

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5.0

Aeolian Islands in style! Only for four

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€1,000

Per person

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4.8

Week 2 June at the Egadi Islands between Nature, Relaxation & Fun

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+5 travellers

have booked

€645

Per person

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4.0

All-inclusive Sardinia & Corsica Cruise (per cabin)

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+106 travellers

have booked

€1,790

Per person

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4.6

Aeolian Islands snorkling and catamaran trekking

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

€675

€750

Per person

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4.9

A week in the Aeolian Islands - 6 islands in 7 days

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+3 travellers

have booked

Starting from

€495

€550

Per person

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4.5

Sailing holiday with maximum comfort

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+6 travellers

have booked

Starting from

€360

Per person

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4.8

Week in Southern Sardinia - Science of Happiness on board

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

€711

€790

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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