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Yacht sailing holidays & skippered tours in Italy

Discover more than 144 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

144

experiences

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4.6

May Day Long Bridge between Tuscany and Corsica

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€380

Per person

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5.0

May 1st in the waters between the Tuscan coast and the Island of Elba

Duration:

1 day - 1 night

Italy:

Tuscany

Give this experience a try!

€90

€95

Per person

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Tour in the marine protected area of Tavolara and Cala Moresca

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€70

Per person

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5.0

May Day: I love you Capraia! Only for 4 guests

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€490

Per person

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Sailing day Genoa, Camogli and San Fruttuoso

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€110

Per person

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4.9

Sailing & adventure among the Egadi Islands

Duration:

4 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€450

Per person

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4.5

Sailing day Maddalena Archipelago

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€125

Per person

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4.8

Cruise in the Gulf of Baratti

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€216

€240

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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5.0

Spring on Lake Garda

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+23 travellers

have booked

€99

Per person

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5.0

All inclusive day trip sailing around the Golfo Paradiso - flex dates

Duration:

1 day - 0 nights

Italy:

Liguria

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+12 travellers

have booked

Starting from

€126

€140

Per person

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4.9

Long live May Day!

Duration:

5 days - 4 nights

Italy:

Aeolian Islands

Give this experience a try!

€382

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.

-

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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