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Showing 55 out of 337 trips

Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

£909


4.7 (40 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : Umbria

Undiscovered Villages of Umbria Walk

£969


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 Dolomites

Cycling from the Dolomites to Venice

£1009


4.8 (6 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Italy : Puglia

Journey through Puglia to Matera

£1009


4.8 (8 reviews)

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Self-guided cultural tour

7 nights,
hotel-to-hotel

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Italy : The Bay of Naples

The Islands of Amalfi Walk

£1059


4.6 (12 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Umbria

The Wine Trails of Umbria Cycling

£1129


5.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Italian Lakes

Walking at Lakes Orta and Maggiore

£1379

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+ & 2

Headwater
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Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

£1459


4.6 (10 reviews)

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Trentino

Brenner Pass to Venice Cycling

£1899


5.0 (2 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Sicily

Walking the Highlights of Western Sicily

£999

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Bay of Naples

The Amalfi Coast Walk

£2009


4.8 (87 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Sicily

Volcanoes of Sicily Walk

£1359


4.4 (11 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Bay of Naples

Paths of the Amalfi Coast

£729


4.6 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Bay of Naples

Walking Amalfi's Path of the Gods

£799


5.0 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Veneto

Walking in the Venetian Hills

£849


4.7 (88 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Veneto

Heart of Veneto Cycling

£939


4.8 (72 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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Italy : Puglia

Self Guided Walking in Puglia: From Lecce to Matera

£1009


4.7 (49 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Italy : Veneto

Bolzano, Verona & Venice Ride

£1079


4.7 (18 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Italy : Veneto

Venetian Villas and Vineyards Cycling

£1079


4.7 (57 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Italy : Sicily

Secrets of Sicily Cycling

£1159


4.6 (22 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Tuscany

A Taste of Tuscany Walking

£1169


4.9 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Tuscany

A Taste of Tuscany Cycling

£1219


4.9 (27 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : The Dolomites

Walks in The Italian Dolomites

£1319


4.9 (126 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Sicily

Cycling through Baroque Sicily

£1479


4.4 (20 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Dolomites

Walking the Dolomites of Alta Badia

£1479


4.8 (23 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Slovenia

Julian Alps to the Adriatic Cycling

£1889


4.8 (118 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Puglia

Contrasts of Puglia Cycling

£1279


4.6 (123 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Piedmont

Gastronomic Barolo Walk

£1909


4.9 (91 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

£2299


4.8 (88 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

£719

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Liguria

Walking in the Cinque Terre and Portofino

£779


4.3 (7 reviews)

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Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Navigation App

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Italy : Puglia

Undiscovered Puglia Walk - Discovering the South-East Coast

£829


4.6 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Italy : The Dolomites

Cross country skiing in the Dolomites

£899

NEW FOR 2025

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Winter snow holiday

7 nights,
single centre

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Italy : Italian Lakes

Cycling Lake Garda with e-bike

£929


4.5 (2 reviews)

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Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Sardinia

Walking Sardinia's Green Coast

£929

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Veneto

Adriatic Coast - Venice to Poreč Ride

£959

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Campania

Coastal Cilento Walk

£1019


4.8 (5 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : The Bay of Naples

Gems of the Amalfi Coast Walking

£1029


4.7 (3 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Umbria

Walking on the Francigena Way

£1079


4.6 (11 reviews)

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Self-guided pilgrimage

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Tuscany

Cycling in Tuscany: Pisa to Florence

£1089


4.6 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Tuscany

Wine & Walk in Chianti

£1109


4.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

£1359

NEW FOR 2025

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Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

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Italy : Emilia Romagna

Emilia Romagna – Bologna to Parma Cycling

£1439


4.7 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Sicily

Sicily: Vino & Volcanoes

£1439

 
 

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Self-guided cultural tour

7 nights,
hotel-to-hotel

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Italy : Sardinia

Undiscovered Sardinia Cycling

£1459


4.7 (19 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Italy : Italian Lakes

Cycling the Italian Lakes

£1649


4.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Puglia

Highlights of Puglia Cycling

£1869


4.8 (11 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Piedmont

Walking the Wine Villages of Piedmont

£2049


4.5 (4 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Piedmont

Cycling the Wine Villages of Piedmont by e-bike

£2199


4.8 (5 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : The Bay of Naples

Walking the Amalfi Coast

£1399


4.7 (6 reviews)

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Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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Italy : Veneto

Walk The Prosecco Hills & Hidden Venice

£1549


4.8 (5 reviews)

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Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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Italy : Puglia

Walking in Puglia & Matera

£1599


4.3 (12 reviews)

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Italy : Sardinia

Walking in Sardinia

£1599


5.0 (1 reviews)

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Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

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Italy : The Dolomites

Snowshoeing in the Dolomites - Premium Adventure

£1799

 
 

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Winter snow holiday

7 nights,
single centre

Printed route
directions

Operated by
Exodus Travels

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Italy : The Dolomites

Classic Dolomites - Premium

£2099


5.0 (1 reviews)

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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.