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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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4.8

Midweek special on the island of Elba, 2 nights

Duration:

3 days - 2 nights

Italy:

Tuscany

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22 travellers

Starting from

€247

€260

Per person

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4.8

Enjoy: in the blue painted blue of the Aeolian Islands

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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142 travellers

Starting from

€475

€500

Per person

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4.6

Long weekend of whale watching with WWF guide between Golfo Paradiso and Gulf of Tigullio

Duration:

3 days - 3 nights

Italy:

Liguria

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18 travellers

Starting from

€389

€409

Per person

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4.5

The most beautiful corners of Sardinia on a Catamaran

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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12 travellers

Starting from

€950

€1,000

Per person

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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi and Sorrento Coast

Duration:

3 days - 2 nights

Italy:

Naples & Amalfi Coast

Give this experience a try!

Starting from

€822

€865

Per person

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5.0

Midweek getaway between Elba and Capraia

Duration:

3 days - 2 nights

Italy:

Tuscany

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19 travellers

Starting from

€333

€350

Per person

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4.0

The hidden jewels of the Aeolian Islands sailing from Palermo

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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39 travellers

Starting from

€451

€475

Per person

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5.0

North and south Sardinia of Corsica sailing

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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26 travellers

Starting from

€475

€500

Per person

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5.0

A day sailing in the fantastic Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

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35 travellers

Starting from

€94

€99

Per person

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4.6

Premium

All-inclusive Sardinia & Corsica Cruise (per cabin)

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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256 travellers

Starting from

€1,026

€1,080

Per person

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4.6

Whale watching cruise with WWF guide between Elba, Pianosa and the canyons of Corsica

Duration:

6 days - 6 nights

Italy:

Tuscany

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22 travellers

Starting from

€929

€978

Per person

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4.8

Aeolian Islands: well-being, taste and fun

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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35 travellers

Starting from

€646

€680

Per person - min 2 pax

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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