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Monohull yacht sailing holidays & tours in Italy

Discover more than 430 opportunities to get on board a Monohull adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

430

experiences

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4.8

Let's discover the Aeolian Islands together by sailing

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+23 travellers

have booked

Starting from

€625

Per person

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Dream Aeolian Islands

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€540

€600

Per person

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5.0

Venice and the Venetian Lagoon

Duration:

2 days - 2 nights

Italy:

Venice and the Gulf of Trieste

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+4 travellers

have booked

€188

Per person

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5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+6 travellers

have booked

Starting from

€433

Per person

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4.9

In the blue between Sardinia and Corsica on a sailboat

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+111 travellers

have booked

Starting from

€650

Per person

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4.8

Aeolian Islands: wellness, taste and fun

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+12 travellers

have booked

Starting from

€551

€580

Per person

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5.0

Sea, sailing and relaxation in the beautiful Aeolian archipelago

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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Mauro

has booked

Starting from

€333

Per person

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3.5

Egadi Islands, Zingaro Nature Reserve, San Vito lo Capo

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+2 travellers

have booked

Starting from

€585

€650

Per person

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4.8

Scopello, San Vito and Egadi: friends, good food sailing

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+12 travellers

have booked

Starting from

€523

€550

Per person

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Intro sail Liguria

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€125

Per person

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4.8

Sorrento Coast, Capri, Positano, Amalfi. Inclusive.

Duration:

3 days - 2 nights

Italy:

Amalfi Coast

Give this experience a try!

Starting from

€550

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

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 - Monohull yacht sailing holidays & tours in Italy

10018 reviews

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25 April - 4 days sailing between La Maddalena and Bonifacio

05/3/2024

Bart S.

-

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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