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Crewed yacht sailing holidays & tours in Italy

Discover more than 51 opportunities to get on board a Crewed adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

51

experiences

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5.0

Sail & Climb in Trieste

Duration:

3 days - 2 nights

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

€420

Per person

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4.0

Pasqua a Vela in Sardegna con Hostess

Duration:

4 days - 3 nights

Italy:

Southern Sardinia

Give this experience a try!

€400

Per person

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4.3

Easter and Easter Monday 2024 aboard a 22-meter boat

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

€600

Per person

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5.0

An all-inclusive day on a sailing boat

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€180

Per person

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5.0

3 DAYS 2 NIGHTS Sailing the Ligurian Coast from GENOVA

Duration:

3 days - 2 nights

Italy:

Liguria

Give this experience a try!

Starting from

€324

€360

Per person

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4.9

25 April between Liguria and Côte d'Azur from Imperia - Stewardess on board

Duration:

4 days - 4 nights

Italy:

Liguria

Give this experience a try!

€500

Per person

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5.0

Long weekend of April 25th between sea, land and good food for only 4 guests

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€420

Per person

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4.3

April 25th on Elba - Stewardess on board - 3 Cab./3 Bathrooms

Duration:

3 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€399

Per person

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4.4

Sailing Excursion Alghero ( Skipper + Hostess )

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€90

Per person

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Sailing and relaxation on the Silver Coast, Tuscan Archipelago and Maremma Coast.

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€396

€440

Per person

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4.8

Yoga and catamaran sailing with chef on board

Duration:

4 days - 4 nights

Italy:

Aegadian islands

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+6 travellers

have booked

€490

Per person

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5.0

Fantastic Sailing Boat Holiday between Elba and Corsica

Duration:

6 days - 6 nights

Italy:

Tuscany

Give this experience a try!

€600

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 - Crewed yacht sailing holidays & tours in Italy

547 reviews

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Take part in the 55th Barcolana with everything included

10/11/2023

Peter C.

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Italy

Fantastica esperienza! Nonostante il vento quasi inesistente Alberto e Federica ci hanno fatto sentire tutta l'energia della Barcolana! Grazie!
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Weekend on the Island of Elba...Hostess on board

10/9/2023

Barbara B.

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Italy

la professionalità e la compagnia di Vittorio e Giulia ci hanno regalato un week end bellissimo. Affidabili, super disponibili e divertenti Consigliatissimo!!!
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All inclusive weekend in the Gulf of Alassio

10/6/2023

John C.

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Italy

Sarà stata la sfortuna o l’improvvisazione ma non abbiamo navigato con Daniele e nonostante l’impegno di Carmen il we “non ha girato” (barca bloccata in porto da “problemi burocratici”) Mi spiace ma non riproverò
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From the Egadi Islands to the Cous Cous Fest of San Vito Lo Capo on a 16-metre boat (private bathroom) with Hostess

10/6/2023

genevieve s.

-

Australia

Amazing trip with the best crew! Highly recommended.

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