Independent walking in Italy

Showing 24 out of 329 trips



Here is our range of independent walking holidays in Italy

These give you maximum flexibility as you travel at your own pace. Our independent walking holidays in Italy let you set off whenever youre ready, choose when and where to stop for lunch, and plan the day around your own personal agenda. We have a wide range of independent walking holidays to choose from: Venetia, Tuscany and Chianti on the mainland, or the islands of Sardinia, Sicily and Capri - plus many other destinations. Simply follow the links below for further details on any of our indepndent walking holidays in Italy.

Click on the appropriate 'View Holiday' button for full holiday details, take a look at our activities section for further information about how our independent walking holidays work, or find out moure about our activity holidays in Italy.

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Italy : Umbria

Undiscovered Villages of Umbria Walk

NZ$2355


4.8 (11 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : The Bay of Naples

The Islands of Amalfi Walk

NZ$2440


4.6 (12 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : Italian Lakes

Walking at Lakes Orta and Maggiore

NZ$3300

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+ & 2

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Italy : Sicily

Walking the Highlights of Western Sicily

NZ$2485

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
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Italy : The Bay of Naples

The Amalfi Coast Walk

NZ$4885


4.8 (87 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : Sicily

Volcanoes of Sicily Walk

NZ$3365


4.4 (11 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : The Bay of Naples

Paths of the Amalfi Coast

NZ$1825


4.6 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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Italy : The Bay of Naples

Walking Amalfi's Path of the Gods

NZ$1980


5.0 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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Italy : Veneto

Walking in the Venetian Hills

NZ$2400


4.7 (88 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Italy : Puglia

Self Guided Walking in Puglia: From Lecce to Matera

NZ$2575


4.7 (52 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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Italy : Tuscany

A Taste of Tuscany Walking

NZ$2795


4.9 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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Italy : The Dolomites

Walks in The Italian Dolomites

NZ$2990


4.9 (126 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
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Italy : The Dolomites

Walking the Dolomites of Alta Badia

NZ$3475


4.8 (23 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
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Italy : Piedmont

Gastronomic Barolo Walk

NZ$3980


4.9 (92 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

NZ$1805

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
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Italy : Liguria

Walking in the Cinque Terre and Portofino

NZ$1850


4.3 (7 reviews)

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Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Navigation App

Italy : Puglia

Undiscovered Puglia Walk - Discovering the South-East Coast

NZ$2070


4.6 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Italy : Istria

Walking the Highlights of Istria: Italy, Slovenia & Croatia

NZ$2200

NEW FOR 2025

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Sardinia

Walking Sardinia's Green Coast

NZ$2265

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : Campania

Coastal Cilento Walk

NZ$2485


4.8 (6 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : The Bay of Naples

Gems of the Amalfi Coast Walking

NZ$2620


4.8 (4 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
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Italy : Tuscany

Wine & Walk in Chianti

NZ$2660


4.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Italy : Piedmont

Walking the Wine Villages of Piedmont

NZ$3300


4.5 (4 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : Umbria

Walking on the Francigena Way

NZ$2685


4.6 (11 reviews)

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Self-guided pilgrimage

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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    Independent walking in Italy

    Overall customer rating, based on 601 reviews

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Where appropriate, we grade our holidays based on distance, terrain, elevation gain, remoteness, etc and categorise them into 4 relative groups. This is ultimately subjective and may vary slightly day to day; for more advice, please see the specific trip page or call one of our friendly team.