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Yacht sailing holidays & skippered tours in Italy

Discover more than 175 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

175

experiences

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4.8

Week in the north of Corsica, via Capraia - in company

Duration:

7 days - 6 nights

Italy:

Tuscany

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20 travellers

€846

€890

Per person

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5.0

Super!

South Sardinia

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

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100 travellers

Starting from

€751

€790

Per person

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4.6

Dolphins & Whales cruise with WWF guide – Ligurian Sea

Duration:

5 days - 6 nights

Italy:

Liguria

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56 travellers

Starting from

€729

€767

Per person

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4.8

ENJOY: in the blue painted blue of the Aeolian Islands

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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85 travellers

Starting from

€475

€500

Per person

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4.9

Sailing & adventure in the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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65 travellers

Starting from

€713

€751

Per person

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5.0

Discovering the Aeolian Islands

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€750

Per person

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5.0

Tour of Elba and Capraia on a Catamaran

Duration:

7 days - 6 nights

Italy:

Tuscany

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Rosario C.

Starting from

€1,100

Per person

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5.0

Super!

Settimana in barca a vela tra Toscana e Corsica

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

€1,500

Per person

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4.4

Enjoy the Aeolian Islands with skipper and hostess

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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58 travellers

Starting from

€940

Per person

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4.0

15 days wandering in the southern Tyrrhenian Sea

Duration:

15 days - 15 nights

Italy:

Aeolian Islands

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2 travellers

€1,950

Per person

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5.0

Super!

Fun and relaxation on a sailing boat

Duration:

8 days - 7 nights

Italy:

Tuscany

Give this experience a try!

€870

Per person

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7 islands in comfort and convenience

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€600

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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