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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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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Duration:

6 days - 7 nights

Italy:

Tuscany

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115 travellers

Starting from

€714

€793

Per person

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Women's sailing

Duration:

2 days - 1 night

Italy:

Tuscany

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5 travellers

Starting from

€177

€197

Per person

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Experience in the Egadi Islands: A Dream on a Sailing Boat

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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16 travellers

Starting from

€360

€400

Per person

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4.9

Week of sea, nature and fun in the Egadi Islands!

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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6 travellers

Starting from

€621

€690

Per person

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4.7

The Egadi Islands as you've never seen them before on a 16-meter boat with a professional hostess

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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87 travellers

€1,332

€1,460

Per person

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4.8

Amalfatina and Phlegraean Coast up to the Pontine

Duration:

7 days - 7 nights

Italy:

Naples & Amalfi Coast

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5 travellers

€1,099

€1,199

Per person

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5.0

Long weekend among the queens of the archipelago - Elba and Capraia

Duration:

4 days - 3 nights

Italy:

Tuscany

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108 travellers

Starting from

€409

€430

Per person

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4.9

Super!

The pearls of the Tyrrhenian Sea: Capri, Ischia, Procida, Ventotene and the Amalfi Coast

Duration:

6 days - 7 nights

Italy:

Naples & Amalfi Coast

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4 travellers

€941

€990

Per person

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4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, and Sorrento

Duration:

5 days - 5 nights

Italy:

Naples & Amalfi Coast

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10 travellers

Starting from

€1,059

€1,115

Per person

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5.0

Week among the queens of the archipelago - Elba, Capraia and Corsica

Duration:

7 days - 6 nights

Italy:

Tuscany

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2 travellers

€998

€1,050

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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21 travellers

Starting from

€475

€500

Per person

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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

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.

-

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.

-

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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