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Yacht sailing holidays & skippered tours in Italy

Discover more than 145 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

145

experiences

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4.8

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

Starting from

€713

€750

Per person

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5.0

Blue Summer Week in Elba and Capraia

Duration:

6 days - 7 nights

Italy:

Tuscany

Give this experience a try!

€867

Per person

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4.9

A week in the Aeolian Islands - 6 islands

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

€800

Per person

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4.7

Discovering the Tyrrhenian Sea: Elba and the Cinque Terre

Duration:

6 days - 7 nights

Italy:

Liguria

Give this experience a try!

€702

€780

Per person

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5.0

On board with the chef at the Egadi Islands

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+25 travellers

have booked

Starting from

€810

€900

Per person

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4.9

Sailing to discover north-western Sicily

Duration:

6 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

€1,000

Per person

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4.6

Flotilla Different: Party and new friends in the Aeolian Islands

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+5 travellers

have booked

Starting from

€999

€1,175

Per person

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4.9

Day on Lake Maggiore

Duration:

1 day - 0 nights

Italy:

Lake Maggiore

Give this experience a try!

€130

Per person

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5.0

Aeolian Islands - Unforgettable cruise among the 7 pearls of the Mediterranean

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+34 travellers

have booked

Starting from

€898

€998

Per person

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4.9

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+30 travellers

have booked

Starting from

€950

Per person

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4.8

Whale watching cruise with WWF on a 22mt boat between Pontine and Ischia

Duration:

6 days - 7 nights

Italy:

Pontine Islands

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+12 travellers

have booked

Starting from

€1,029

Per person

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4.9

Magical week at the Egadi Islands on a new catamaran

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+28 travellers

have booked

Starting from

€1,400

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

10888 reviews

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A weekend of sailing between Capraia and the island of Elba

03/20/2024

davide C.

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Italy

Enrico è un comandante che sa mettervi a proprio agio in un equilibrio di libertà e professionalità . Se vi piace oltre al vento il buon cibo siete sulla barca giusta ..
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Ventotene by sailing boat from Naples

10/16/2023

Manuela M.

Come chiudere “l’estate” in bellezza? Con un week da sogno a Ventotene con Gennaro ed Emiliano! Le aspettative non vengono mai disattese …e ci salutiamo sperando nella benevolenza del meteo per poter dire la settimana prossima… noi siamo ancora qui! L’estate non è finita! Incrociamo le dita!
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Weekend of sea and colors between Ischia, Procida, Vivara and the Phlegraean fields

10/16/2023

Manuela M.

Quando vuoi avere la certezza di passare un eccellente week and a vela …..non puoi che scegliere Gennaro ed Emilano! Compagni di viaggio ke diventano amici, cibo eccellente preparato con amore dalla ormai carissima Raffaella, richieste improbabili tutte accontentate, barca sempre al top ma soprattutto loro, Gennaro ed Emiliano che fanno la differenza!
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Aeolian Islands in Blue between sea and sky: Sun, sport, music, good food ... The rest is magic!

10/16/2023

Damien B.

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Switzerland

It was my first excursion by boat and it was an incredible experience! I can only recommend it! The landscapes are beautiful and the boat is well-maintained with enough space and a nice Skipper. ++ Dario knows a lot about the sea and his boat! He likes to share what he knows about it. He knows also when to integrate the group and when to let things happen. He likes humans and is very kind. During, before and after he was also very reachable. -- I would have appreciated more information and clarity about excursions. I added them below to help the comments readers. ?? Be aware of taking good shoes, warm clothes and a torch if you want to climb the Stromboli (which I highly recommend) There is the possibility of eating in restaurants on different islands. Being barefoot is recommended on the boat. Bring your eco-shampoo with you. The bedsheets were furnished. Hope that's help and that you will enjoy the tour!

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