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Yacht sailing holidays & skippered tours in Italy

Discover more than 130 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

130

experiences

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4.5

Weekend YOGA in barca a vela

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€370

Per person

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5.0

Weekend of relaxation and fun

Duration:

2 days - 2 nights

Italy:

Liguria

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+23 travellers

have booked

€280

€295

Per person

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4.7

Two hearts and a sailboat: discovering the Phlegrean Islands

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

Give this experience a try!

Starting from

€250

Per person

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4.8

DISCOVERING THE EGADI ISLANDS on the Routes of the Florio Family

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+2 travellers

have booked

€727

€765

Per person

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W.E Golfo Dei Poeti-Portovenere-Rosse-Ferale

Duration:

2 days - 2 nights

Italy:

Liguria

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+44 travellers

have booked

€190

Per person

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4.8

Cruise in the Gulf of Baratti

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€216

€240

Per person

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4.8

Weekend on a sailing boat in ALASSIO

Duration:

2 days - 1 night

Italy:

Liguria

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+2 travellers

have booked

€270

Per person

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5.0

Wonderful holiday sailing between Elba and Giglio

Duration:

7 days - 7 nights

Italy:

Tuscany

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+2 travellers

have booked

€850

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!

€500

Per person

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4.9

Sailing & Adventure in the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+36 travellers

have booked

Starting from

€646

€680

Per person

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5.0

A sailing holiday for two in northern Sardinia and southern Corsica

Duration:

6 days - 6 nights

Italy:

Northern Sardinia

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+2 travellers

have booked

€850

Per person

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4.9

Beautiful bays between North Sardinia and South Corsica on a catamaran

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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+33 travellers

have booked

€846

€940

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.

-

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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