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Yacht sailing holidays & skippered tours in Italy

Discover more than 238 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

238

experiences

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4.8

The Egadi Islands as you've never seen them before on a 16-meter boat with hostess

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+41 travellers

have booked

Starting from

€799

Per person

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4.5

Egadi, a paradise for sailing and snorkelling

Duration:

7 days - 8 nights

Italy:

Aegadian islands

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+38 travellers

have booked

Starting from

€600

Per person

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5.0

Cruise to the Island of Elba and Capraia

Duration:

6 days - 7 nights

Italy:

Tuscany

Give this experience a try!

€1,200

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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+49 travellers

have booked

Starting from

€870

Per person

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5.0

Enjoy: nel blu dipinto di blu delle Eolie

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+54 travellers

have booked

Starting from

€466

€490

Per person

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4.6

North Sardinia - La Maddalena and Costa Smeralda

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+14 travellers

have booked

Starting from

€600

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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4.8

One Way: Elba - Corsica - Sardinia with suggestive night crossing

Duration:

5 days - 6 nights

Italy:

Northern Sardinia

Give this experience a try!

€550

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

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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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

€750

Per person

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Mini cruise Syracuse - Marzamemi

Duration:

3 days - 2 nights

Italy:

Sicily

Give this experience a try!

€801

€890

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

10907 reviews

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25 April - 4 days sailing between La Maddalena and Bonifacio

05/3/2024

Bart S.

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Spain

Excellent sailing trip in a comfortable boat with a great captain!! Grazie per tutto Leo & Crew!!!
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Sailing, early sun and aperitif at sunset ... What else?

05/3/2024

Cristiana L.

-

Italy

Giornata stupenda! lo skipper Emanuele molto simpatico, alla mano e soprattutto molto preparato e affidabile. Abbiamo veleggiato con un bel vento, io sono interessata alla vela ed Emanuele mi ha spiegato tante cose, fatto fare delle manovre e riposto pazientemente a tutte le mie tante domande. Abbiamo anche fatto un bellissimo aperitivo all'ancora. Non posso che consigliare vivamente questa esperienza!
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May 1st on Elba - Stewardess on board -3 Cab./ 3 Bathrooms

05/2/2024

susanna s.

-

Italy

una splendida vacanza . Fabio e Angela gentilissimi mi hanno offerto ogni confort a bordo e insegnato i primi rudimenti della vela .
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25 April - Whale watching expedition with WWF researcher in Liguria

05/2/2024

Rossella D.

-

Italy

Esperienza complessivamente decisamente positiva, nonostante le importanti difficoltà causate dalle pessime condizioni meteorologiche. L'estrema professionalità dello skipper e delle guide di whale watching, insieme al grande affiatamento e collaborazione che si è creato con tutto l'equipaggio, hanno fatto in modo che l'intera esperienza si vivesse nel migliore dei modi, in totale armonia, portando a casa anche grandi soddisfazioni di avvistamento di delfini, balenottere e tartarughe! Un'esperienza davvero indimenticabile, grazie di cuore!

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