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Yacht sailing holidays & skippered tours in Italy

Discover more than 197 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

197

experiences

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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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4.8

Super!

Large Luxury Catamaran with Hostess - Discovering the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

€1,251

€1,390

Per person

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4.7

1st One-Way Special - Between the island of Elba, Corsica and Sardinia

Duration:

6 days - 6 nights

Italy:

Northern Sardinia

Give this experience a try!

€774

€860

Per person

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5.0

Talamone and Giglio Sailing Weekend with Geniale Vento, Mare, Libertà

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€405

€450

Per person

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4.8

Vacanza a piedi nudi: Weekend tra Elba e Capraia su barca 15m

Duration:

2 days - 2 nights

Italy:

Tuscany

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37 travellers

Starting from

€225

€250

Per person

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4.9

Unforgettable Catamaran Cruise in Elba, Capraia and Corsica

Duration:

7 days - 6 nights

Italy:

Tuscany

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30 travellers

Starting from

€984

€1,093

Per person

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4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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37 travellers

Starting from

€477

€530

Per person

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4.8

Super!

Aeolian Islands - Large and new catamaran equipped with every comfort

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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2 travellers

Starting from

€882

€980

Per person

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5.0

Aeolian Islands: between sea and authentic flavours

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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123 travellers

Starting from

€585

€650

Per person

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5.0

Super!

Weekend between the Gargano and the Tremiti

Duration:

2 days - 2 nights

Italy:

Tremiti Islands

Give this experience a try!

€284

€315

Per person

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5.0

Sailing for a weekend at Elba Island - Spring/Summer

Duration:

3 days - 2 nights

Italy:

Tuscany

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6 travellers

€261

€290

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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