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Yacht sailing holidays & skippered tours in Italy

Discover more than 153 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

153

experiences

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4.5

A week with YOGA and SAILING lessons in the Tuscan Archipelago

Duration:

7 days - 7 nights

Italy:

Tuscany

Give this experience a try!

€1,350

Per person

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Sailing weekend in Camogli and Portofino from Genoa

Duration:

2 days - 1 night

Italy:

Liguria

Give this experience a try!

€199

Per person

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5.0

The island of Ischia between sailing and trekking

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

Give this experience a try!

€200

Per person

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5.0

Weekend with wine tasting between Santa Margherita Ligure and Portofino

Duration:

2 days - 2 nights

Italy:

Liguria

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+12 travellers

have booked

Starting from

€332

€390

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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4.8

Sailing on Elba

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€324

€360

Per person

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Fine Settimana in Liguria - All inclusive

Duration:

2 days - 2 nights

Italy:

Liguria

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+21 travellers

have booked

€380

Per person

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5.0

Sailing day in the Ligurian nature, boarding from Varazze

Duration:

1 day - 0 nights

Italy:

Liguria

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chiara c.

has booked

Starting from

€95

Per person

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5.0

Sailing in Ventotene

Duration:

2 days - 1 night

Italy:

Pontine Islands

Give this experience a try!

€220

Per person

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Bachelorette Party

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

Starting from

€162

€170

Per person

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4.5

SAIL ACADEMY - Varazze

Duration:

2 days - 1 night

Italy:

Liguria

Give this experience a try!

€230

Per person

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5.0

Free in the Wind... scents and wonders in the upper Adriatic

Duration:

2 days - 1 night

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

€188

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

10894 reviews

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A weekend of sailing between Capraia and the island of Elba

04/24/2024

Angelo C.

-

Italy

Bellissima esperienza, bella gente con uno skipper top!
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Easter on the Island of Elba

04/22/2024

Antonios S.

-

Italy

Anche se il tempo non ha aiutato, è stata una bellissima esperienza
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Trekking and sailing weekend on the island of Elba

04/22/2024

Sara C.

-

Italy

Bellissima esperienza,grazie alla cordialità e professionalità di Marco e i compagni di avventura. Ho apprezzato molto anche la possibilità di fare trekking. Consigliatissimo!!
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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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