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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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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

€919

Per person

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South Sardinia

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

€874

€920

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

€700

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

€450

Per person

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4.8

Little sailors grow up: 5 days sailing on the island of Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

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+3 travellers

have booked

€490

Per person

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4.8

Sail & Tour: Sorrento, Capri, Positano, Amalfi - with 2 nights in villa

Duration:

5 days - 4 nights

Italy:

Amalfi Coast

Give this experience a try!

€995

Per person

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4.8

All in the Family: 5 days sailing on Elba on a comfortable 17m boat

Duration:

4 days - 4 nights

Italy:

Tuscany

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+7 travellers

have booked

€490

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

Starting from

€740

Per person

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The Aeolian Islands in an exclusive boat

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+4 travellers

have booked

Starting from

€800

Per person

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5.0

An all-inclusive day on a sailing boat

Duration:

1 day - 0 nights

Italy:

Liguria

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+14 travellers

have booked

€180

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

€820

Per person

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4.9

Between sunsets and aperitifs on a sailing boat

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

€583

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

10896 reviews

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Long weekend of April 25 in Elba, Corsica and Capraia

04/29/2024

Paolo G.

-

Italy

Bellissima esperienza all’isola d’Elba, che non conoscevo e ho cominciato ad amare. Paolo è semplicemente fantastico! Divertente e sicuro nel condurre la barca, tutto ciò che si cerca in uno skipper. Ha saputo conciliare le esigenze di tutti, ci ha fatto andare a vela ma anche rilassare, sempre in sicurezza. Nel mangiare e fare aperitivi è un fuoriclasse! Un ponte del 25 aprile da ricordare!
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Long weekend of April 25 in Elba, Corsica and Capraia

04/29/2024

Laurent M.

-

France

seul Francais a bord ne parlant pas italien avec des co-equipiers italiens, mais passionné de voile et voulant apprendre l'italien, le Capitaine Paolo a ete genialissime pour aider a m'integrer avec toutes les langues qu'il parle, supers sessions de voiles, tres belles etapes dans les marinas, et dolce vita avec tout l'équipage: j'ai adoré ces 4 jours et je repars avec toute une bande de nouveaux amis italiens !!! Paolo, je reviens des que je peux !!! Ciao a tutti amici !!!
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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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