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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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4.0

Conquering the Aeolian Islands - Cook on board

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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33 travellers

Starting from

€625

Per person

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4.9

Super!

Long weekend between Amalfi, Positano and Capri

Duration:

3 days - 2 nights

Italy:

Naples & Amalfi Coast

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6 travellers

€380

Per person

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Weekend in barca a vela a Marina di Ravenna

Duration:

2 days - 1 night

Italy:

Central Adriatic

Starting from

€133

Per person

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4.8

Two hearts and a sailboat: discovering the Phlegrean Islands

Duration:

2 days - 2 nights

Italy:

Naples & Amalfi Coast

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11 travellers

€312

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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13 travellers

Starting from

€689

Per person

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5.0

Prime fughe primaverili in compagnia del mare

Duration:

2 days - 2 nights

Italy:

Liguria

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17 travellers

Starting from

€275

Per person

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Weekend Portovenere and Golfo, convenient boarding in La Spezia

Duration:

2 days - 2 nights

Italy:

Liguria

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6 travellers

Starting from

€300

Per person

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5.0

Weekend at the Pontine - two schooners in company

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€270

Per person

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5.0

Midweek relaxing in the Pontine Mountains

Duration:

4 days - 3 nights

Italy:

Pontine Islands

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53 travellers

Starting from

€337

Per person

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4.4

Week in the Egadi Islands with Hostess on board

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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2 travellers

€830

Per person

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Sailing among the Egadi Islands

Duration:

3 days - 2 nights

Italy:

Aegadian islands

Give this experience a try!

€260

Per person

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4.8

Super!

All Inclusive - Procida, Ischia, Capri: the Pearls of the Gulf

Duration:

3 days - 2 nights

Italy:

Naples & Amalfi Coast

Give this experience a try!

€680

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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