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Yacht sailing holidays & skippered tours in Italy

Discover more than 182 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

182

experiences

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4.8

Super!

Lampedusa, Lampione e Linosa fra colori magici

Duration:

7 days - 7 nights

Italy:

Pantelleria and Lampedusa

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34 travellers

€595

€700

Per person

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4.7

Two boats walking on the island of Elba: the magic of the roadstead!

Duration:

6 days - 5 nights

Italy:

Tuscany

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2 travellers

Starting from

€638

€750

Per person

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4.6

Cruise to the Maddalena Archipelago and South Corsica

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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30 travellers

Starting from

€667

€785

Per person

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5.0

Poetic Gulf of Poets

Duration:

3 days - 2 nights

Italy:

Liguria

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18 travellers

Starting from

€170

€200

Per person

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Two boats walking on the island of Elba: the magic of the roadstead!

Duration:

6 days - 5 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€850

€1,000

Per person

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4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Duration:

3 days - 3 nights

Italy:

Tuscany

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18 travellers

Starting from

€342

€380

Per person

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4.3

Sailing holiday in the archipelago of La Maddalena and Costa Smeralda

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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4 travellers

Starting from

€720

€800

Per person

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4.9

From the Pontine to the Egadi Islands - Adventure, Navigation, and Relaxation - One Way

Duration:

6 days - 6 nights

Italy:

Aegadian islands

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2 travellers

€531

€590

Per person

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5.0

Weekend in Ogliastra, super Sardinia with skipper and hostess

Duration:

3 days - 2 nights

Italy:

Southern Sardinia

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12 travellers

€612

€680

Per person

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4.9

Super!

Midweek on Elba, from Monday to Thursday

Duration:

3 days - 3 nights

Italy:

Tuscany

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23 travellers

Starting from

€356

€395

Per person

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4.3

Sailing in the natural parks of Sardinia, from La Maddalena to Asinara

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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2 travellers

€810

€900

Per person

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Sailing Cruise - The Odyssey - Egadi Islands - Sicily

Duration:

6 days - 6 nights

Italy:

Aegadian islands

Give this experience a try!

€855

€950

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

12220 reviews

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Weekend catamaran in Portovenere and Cinque Terre

05/12/2025

Davide S.

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Italy

Antonio ed il suo catamarano "Cassiopea" sono il perfetto mix tra compentenza, professionalità, freschezza, passione e disponibilità nel far sentire gli ospiti a loro agio durante tutta la permanenza in barca. Semplicemente quello che serve per staccare la spina dalla frenesia quotidiana e trascorrere dei bei momenti in mare in ottima compagnia. Super consigliato.
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Weekend in Capraia, the island with timeless sunsets

05/12/2025

Stefano F.

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Italy

Marco è un vero appassionato di barche e, per questo, ti fa assaporare ogni momento che si trascorre a bordo
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Stuffed anchovies: magical weekend from Genoa

05/12/2025

Maurizio S.

4 stelle perché c’è sempre la possibilità di migliorare, Bella esperienza che va senz’altro rifatta in luoghi diversi.
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1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK

05/8/2025

Maria Pia D.

-

Italy

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