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Yacht sailing holidays & skippered tours in Italy

Discover more than 28 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

28

experiences

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4.9

Veleggiate e aperitivi all'Elba e isole vicine

Duration:

3 days - 2 nights

Italy:

Tuscany

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+6 travellers

have booked

Starting from

€333

Per person

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4.9

Capraia under full sail / trekking on the island

Duration:

3 days - 2 nights

Italy:

Tuscany

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+4 travellers

have booked

€240

Per person

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The hidden jewels of the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+20 travellers

have booked

€390

€410

Per person

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4.8

Seductive weekend on a sailing boat on the island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+8 travellers

have booked

€239

€265

Per person

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4.5

Weekend of sea and colors between Ischia, Procida and Vivara

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

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+12 travellers

have booked

€237

€249

Per person

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4.9

Basic sailing course on cabin cruisers

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€225

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!

€225

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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5.0

An all-inclusive day on a sailing boat

Duration:

1 day - 0 nights

Italy:

Liguria

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+11 travellers

have booked

€180

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+21 travellers

have booked

€730

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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+104 travellers

have booked

Starting from

€1,701

€1,790

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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Daniela

has booked

€450

€500

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

10891 reviews

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Luxury sailing in the Gulf of Poets

04/15/2024

Antonio C.

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Italy

Giornata splendida, mare e barca perfetti, altissimo valore aggiunto l’equipaggio, simpatico gentile preparato ma soprattutto disponibile, e Costanza ottima cuoca, esperienza fantastica, da ripetere!!
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Veleggiata verso il farò di Cecina con Aperitivo a bordo

04/11/2024

maurizio r.

-

Italy

Grazie per la bella domenica di relax in barca Maurizio e Giuliana
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Moorings and manoeuvres course - Night Navigation and Signals - Anchorages

04/10/2024

Stefano P.

-

Italy

Corso vela, efficace, utilissimo, sintetico essenziale in una parola strepitoso. Skipper istruttore preparato, simpatico ed all'altezza del ruolo.
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A weekend of sailing between Capraia and the island of Elba

03/20/2024

davide C.

-

Italy

Enrico è un comandante che sa mettervi a proprio agio in un equilibrio di libertà e professionalità . Se vi piace oltre al vento il buon cibo siete sulla barca giusta ..

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