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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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5.0

Holidays in the Egadi Islands

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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+6 travellers

have booked

Starting from

€624

Per person

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Sardinia and Costa Smeralda in Comfort - with Hostess - All Inclusive

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€1,690

Per person

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5.0

Explore Sardinia's coastline! Skipper & Hostess - All included

Duration:

6 days - 6 nights

Italy:

Northern Sardinia

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+13 travellers

have booked

€1,490

Per person

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4.8

Elba Capraia and Caorsica - Sea and Colour

Duration:

6 days - 7 nights

Italy:

Tuscany

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+10 travellers

have booked

Starting from

€520

Per person

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Sailing to discover the Egadi Islands

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+12 travellers

have booked

€562

€624

Per person

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Aeolian Week

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

Give this experience a try!

€750

Per person

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4.6

Aeolian Islands snorkeling and catamaran trekking

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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Asley

has booked

€675

€750

Per person

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5.0

Aeolian Islands in style! Only for four

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€1,000

Per person

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4.0

All-inclusive Sardinia & Corsica Cruise (per cabin)

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+108 travellers

have booked

€1,790

Per person

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4.8

Week 2 June at the Egadi Islands between Nature, Relaxation & Fun

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+5 travellers

have booked

€645

Per person

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4.9

A week in the Aeolian Islands - 6 islands in 7 days

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+8 travellers

have booked

Starting from

€495

€550

Per person

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4.5

Sailing holiday with maximum comfort

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+6 travellers

have booked

Starting from

€360

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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