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Yacht sailing holidays & skippered tours in Italy

Discover more than 148 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

148

experiences

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4.9

Long live May Day!

Duration:

5 days - 4 nights

Italy:

Aeolian Islands

Give this experience a try!

€382

Per person

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Magic charter Sorrento Capri Amalfi Positano

Duration:

4 days - 3 nights

Italy:

Amalfi Coast

Give this experience a try!

€750

Per person

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4.9

North Sardinia and Costa Smeralda onboard of a Catamran

Duration:

5 days - 4 nights

Italy:

Northern Sardinia

Give this experience a try!

€525

Per person

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5.0

May Day on Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€365

Per person

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4.8

1 May - Whale watching expedition with WWF researcher between Lavagna and Portofino

Duration:

4 days - 4 nights

Italy:

Liguria

Give this experience a try!

€449

Per person

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4.8

An unforgettable sail to discover the Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

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+17 travellers

have booked

€350

Per person

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5.0

First dives in the Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

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+11 travellers

have booked

Starting from

€400

Per person

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4.5

Weekend di vela e Trekking all'Isola d'Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+2 travellers

have booked

€280

Per person

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4.9

Capraia under full sail / trekking on the island

Duration:

3 days - 2 nights

Italy:

Tuscany

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+4 travellers

have booked

€265

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!

€400

Per person

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5.0

Relaxing weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+27 travellers

have booked

€265

Per person

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4.9

Weekend at the Pontine Islands: Ponza and Palmarola

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+3 travellers

have booked

Starting from

€240

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

10899 reviews

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Long weekend in Capraia and North Corsica

04/30/2024

Marcello O.

-

Italy

Bel giro tra Capraia e Corsica... e poi abbiamo visto anche le balene al largo della Corsica!!! Marco, lo skipper, dovrebbe scrivere un libro su tutte le sue esperienze vissute che ti racconta tra una bolina e un'altra... Alla prossima!
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Trekking & Sailing Experience 25 Aprile tra Elba e Capraia - 2 barche

04/30/2024

luca f.

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Italy

Esperienza bellissima, nonostante il meteo non abbia consentito di raggiungere Capraia, lo skipper Edoardo ha organizzato con Francesco, la guida trekking, un itinerario molto divertente ed esaustivo dell'isola d'Elba. Edoardo bravo, competente e molto comunicativo, davvero una bella persona!
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Spring long deck by catamaran in Cinque Terre

04/29/2024

Marco S.

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Italy

Grande Antonio! È stato un piacere fare questa esperienza con lui. Ci ha coccolato per tutto il viaggio con la sua cucina buonissima. Persona super disponibile, divertente e piena di risorse. Barca favolosa. Ottima compagnia. Che dire… è stato tutto meraviglioso.
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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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