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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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4.9

Super!

Life Changing Experiences - Week in the Pontine Islands

Duration:

6 days - 6 nights

Italy:

Pontine Islands

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6 travellers

Starting from

€1,000

Per person

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5.0

Pure life in the Aeolian Islands: between volcanoes and crystal clear waters

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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17 travellers

Starting from

€740

Per person

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A sail for rebirth

Duration:

3 days - 2 nights

Italy:

Tuscany

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4 travellers

€320

Per person

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4.9

Super!

Egadi paradise for sailing and snorkeling

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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66 travellers

Starting from

€600

Per person

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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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4.8

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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4.8

ONE WAY From the Phlegraean to the Pontine Islands

Duration:

8 days - 7 nights

Italy:

Pontine Islands

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9 travellers

Starting from

€660

Per person

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4.8

Settimana alle isole Pontine (scuola vela) 

Duration:

7 days - 6 nights

Italy:

Pontine Islands

Give this experience a try!

€650

Per person

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5.0

Relaxing week in the Pontine Islands

Duration:

7 days - 6 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€1,000

Per person

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5.0

Between seas and volcanoes, fall in love with the Aeolian Islands

Duration:

5 days - 4 nights

Italy:

Aeolian Islands

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26 travellers

€590

Per person

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5.0

Aeolian Islands - Volcanoes, Sail & Trekking - Mountain Guide on board

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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11 travellers

€1,430

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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