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Yacht sailing holidays & skippered tours in Italy

Discover more than 29 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

29

experiences

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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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5.0

Isole Eolie - Mare Sole e Relax su un nuovo e grande Catamarano Lagoon

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+2 travellers

have booked

€1,170

€1,800

Per person

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4.0

Exclusive cruise on the new Lagoon 42 of 2024

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+7 travellers

have booked

Starting from

€573

Per person

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Sailing, Sea and Cuisine in the Aeolian Islands: good food between sailing and sea!

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+7 travellers

have booked

€738

€820

Per person

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4.9

The Maddalena Archipelago by sail.

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+33 travellers

have booked

Starting from

€700

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

€333

Per person

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4.5

1 Week Professional Catamaran Training - Cagliari Sardinia

Duration:

7 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

Starting from

€1,320

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

€523

€550

Per person

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5.0

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+8 travellers

have booked

€1,300

€2,000

Per person

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5.0

North/East Sardinia and South Corsica on a sailing boat with gourmet cuisine

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€900

Per person

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5.0

Summer in the Egadi Islands

Duration:

6 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

€561

€590

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

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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