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Yacht sailing holidays & skippered tours in Italy

Discover more than 196 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

196

experiences

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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

Starting from

€1,986

€2,090

Per person

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4.8

Discovering the Tuscan archipelago and Northern Corsica

Duration:

6 days - 6 nights

Italy:

Tuscany

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+2 travellers

have booked

€1,099

Per person

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5.0

Blue Weeks in Southern Sardinia

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

€850

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

€560

Per person

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5.0

Enjoy: in the blue painted blue of the Aeolian Islands

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+6 travellers

have booked

€790

Per person

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Aeolian Islands on a sailing boat: good food between sailing and sea!

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+12 travellers

have booked

Starting from

€990

€1,100

Per person

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4.8

Egadi Islands - Sea, sun, relax on a brand new catamaran of 2024 - Hostess/cook on board

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+2 travellers

have booked

€1,300

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

€775

Per person

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Eolie a vela con skipper ed hostess, all inclusive con cucina vegana

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+2 travellers

have booked

€1,750

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

€660

Per person

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4.8

Aeolian Islands: wellness, taste, fun with a fabulous cook on board

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+12 travellers

have booked

Starting from

€969

€1,020

Per person

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4.0

Sailing, Relaxation and Fun in the Pontine and Phlegraean Islands on a 15-meter Boat

Duration:

7 days - 7 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€800

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

10908 reviews

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April 25th long weekend in Bastia

05/6/2024

Lisa V.

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Italy

Bellissima esperienza. Lo Skipper Enrico oltre ad essere un ottimo uomo di mare ci ha deliziati di ottimi pranzetti e cene in barca.
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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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