We love all the countries we visit, but there's something special about discovering Italy behind the scenes. We have crafted outstanding walking and cycling holidays in no fewer than ten of Italy's wonderfully diverse regions, each with its own unique geological features, gastronomy and fascinating history.

Taking you firmly off the tourist trail, we explore the medieval castles and alpine villages of Trentino as you cycle from the Dolomites to Lake Garda. Or to truly get your taste buds tingling, why not take a gastronomic tour of Piedmont's famous vineyards, Savoy castles and frescoed chapels and enchanting hilltop towns.

From beautiful strolls through historic towns along the Francigena pilgrimage route and Umbria to scenic cycles through the spectacular fairy-tale regions of Puglia and Matera, all of our Italian holidays are carefully curated to give you a true taste of la dolce vita as you experience the country through the eyes of a local.

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Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

CA$2195


4.7 (44 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Umbria

Undiscovered Villages of Umbria Walk

CA$2235


4.7 (15 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : The Bay of Naples

The Islands of Amalfi Walk

CA$2310


4.6 (14 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

Italy : The Dolomites

Cycling from the Dolomites to Venice

CA$2330


4.6 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Italy : Puglia

Journey through Puglia to Matera

CA$2385


4.8 (13 reviews)

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

Italy : Umbria

The Wine Trails of Umbria Cycling

CA$2540


5.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Trentino

Brenner Pass to Venice Cycling

CA$2995


5.0 (2 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Italian Lakes

Walking at Lakes Orta and Maggiore

CA$3050

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+ & 2

Headwater
Navigation App

Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

CA$3300


4.7 (14 reviews)

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Sicily

Walking the Highlights of Western Sicily

CA$2350

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

Italy : The Bay of Naples

The Amalfi Coast Walk

CA$4420


4.8 (90 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Sicily

Volcanoes of Sicily Walk

CA$3110


4.4 (12 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : The Bay of Naples

Paths of the Amalfi Coast

CA$1780


4.6 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

Italy : The Bay of Naples

Walking Amalfi's Path of the Gods

CA$1910


5.0 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

Italy : Veneto

Heart of Veneto Cycling

CA$2235


4.8 (73 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

Italy : Veneto

Walking in the Venetian Hills

CA$2270


4.7 (90 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Veneto

Bolzano, Verona & Venice Ride

CA$2330


4.7 (20 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Puglia

Self Guided Walking in Puglia: From Lecce to Matera

CA$2425


4.7 (64 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

Italy : Sicily

Secrets of Sicily Cycling

CA$2595


4.6 (24 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Tuscany

A Taste of Tuscany Walking

CA$2615


4.9 (31 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

Italy : Tuscany

A Taste of Tuscany Cycling

CA$2710


4.9 (28 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Italy

Venetian Villas and Vineyards Cycling

CA$2710


4.7 (57 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

Italy : The Dolomites

Walks in The Italian Dolomites

CA$2805


4.9 (127 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : The Dolomites

Walking the Dolomites of Alta Badia

CA$3205


4.8 (23 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Sicily

Cycling through Baroque Sicily

CA$3220


4.5 (22 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Slovenia

Julian Alps to the Adriatic Cycling

CA$4440


4.8 (123 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Puglia

Contrasts of Puglia Cycling

CA$2995


4.6 (125 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Piedmont

Gastronomic Barolo Walk

CA$3640


4.9 (95 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

CA$4075


4.8 (88 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Veneto

Walking in the Prosecco Hills

CA$1685

NEW FOR 2025

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 1+ & 2

Navigation App

Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

CA$1760

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Liguria

Walking in the Cinque Terre and Portofino

CA$1795


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

CA$1985


4.8 (13 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : The Dolomites

Cross country skiing in the Dolomites

CA$2005

NEW FOR 2025

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Winter snow holiday

7 nights,
single centre



Italy : Istria

Walking the Highlights of Istria: Italy, Slovenia & Croatia

CA$2100

NEW FOR 2025

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Italian Lakes

Cycling Lake Garda with e-bike

CA$2160


4.5 (2 reviews)

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Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Sardinia

Walking Sardinia's Green Coast

CA$2255

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Veneto

Adriatic Coast - Venice to Porec Ride

CA$2290

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Campania

Coastal Cilento Walk

CA$2350


4.9 (8 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Tuscany

Cycling in Tuscany: Pisa to Florence

CA$2405


4.6 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : The Bay of Naples

Gems of the Amalfi Coast Walking

CA$2460


4.8 (4 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

Italy : Trentino

Wine & Walk in Chianti

CA$2500


4.0 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Italy : Umbria

Walking on the Francigena Way

CA$2520


4.6 (11 reviews)

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Self-guided pilgrimage

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

CA$2975

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

Italy : Piedmont

Walking the Wine Villages of Piedmont

CA$3050


4.5 (4 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Sardinia

Undiscovered Sardinia Cycling

CA$3145


4.7 (19 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Italy : Emilia Romagna

Emilia Romagna: Bologna to Parma Cycling

CA$3205


4.7 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Sicily

Sicily: Vino & Volcanoes

CA$3260


5.0 (2 reviews)

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

Italy : Piedmont

Cycling the Wine Villages of Piedmont by e-bike

CA$3490


4.8 (5 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Italian Lakes

Cycling the Italian Lakes

CA$3735


4.8 (5 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy

Highlights of Puglia Cycling

CA$4115


4.8 (13 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : The Bay of Naples

Walking the Amalfi Coast

CA$2755


4.7 (11 reviews)

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Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

Italy : Puglia

Walking in Puglia & Matera

CA$2850


4.3 (12 reviews)

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Italy : Sardinia

Walking in Sardinia

CA$2850


5.0 (1 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

Italy : Veneto

Walk The Prosecco Hills & Hidden Venice

CA$2850


4.8 (5 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

Italy : The Dolomites

Snowshoeing in the Dolomites - Premium Adventure

CA$3230

 
 

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Winter snow holiday

7 nights,
single centre

Printed route
directions

Operated by
Exodus Travels

Italy : The Dolomites

Classic Dolomites - Premium

CA$3990


5.0 (1 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

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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.

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