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Showing 52 out of 308 trips

Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

£1039


4.7 (44 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Umbria

Undiscovered Villages of Umbria Walk

£1079


4.7 (16 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Puglia

Journey through Puglia to Matera

£1129


4.8 (15 reviews)

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Cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

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Italy

The Wine Trails of Umbria Cycling

£1149


5.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Dolomites

Cycling from the Dolomites to Venice

£1209


4.6 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Italy : The Bay of Naples

The Islands of Amalfi Walk

£1259


4.6 (14 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Italy / Switzerland

Walking at Lakes Orta and Maggiore

£1519


4.9 (7 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

£1639


4.7 (14 reviews)

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Sicily

Walking the Highlights of Western Sicily

£1159


4.5 (104 reviews)

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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

£2389


4.8 (93 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

£1499


4.4 (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 : Tuscany

A Taste of Tuscany Cycling

£70


4.9 (29 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 Bay of Naples

Walking Amalfi's Path of the Gods

£899


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 : The Bay of Naples

Paths of the Amalfi Coast

£899


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 : Veneto

Heart of Veneto Cycling

£1069


4.8 (73 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

£1109


4.7 (65 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

£1129


4.7 (20 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Veneto

Walking in the Venetian Hills

£1149


4.7 (91 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 : Tuscany

A Taste of Tuscany Walking

£1269


4.9 (31 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Dolomites

Walks in The Italian Dolomites

£1279


4.9 (136 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

Secrets of Sicily Cycling

£1339


4.6 (25 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 : The Dolomites

Walking the Dolomites of Alta Badia

£1469


4.8 (28 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

£1689


4.5 (23 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Slovenia / Italy

Julian Alps to the Adriatic Cycling

£2229


4.8 (128 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

£1449


4.6 (126 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 Cycling by e-bike

£2089


4.8 (89 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Piedmont

Gastronomic Barolo Walk

£2089


4.9 (97 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Veneto

Walking in the Prosecco Hills

£819

NEW FOR 2026

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Liguria

Walking in the Cinque Terre and Portofino

£859


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 : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

£869

 
 

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy

Undiscovered Puglia Walk - Discovering the South-East Coast

£899


4.8 (13 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Sardinia

Walking Sardinia's Green Coast

£1009


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Italian Lakes

Cycling Lake Garda by e-bike

£1029


4.6 (5 reviews)

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Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy / Slovenia / Croatia

Adriatic Coast - Venice to Porec Ride

£1079


4.3 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy / Slovenia / Croatia

Walking the Highlights of Istria: Italy, Slovenia & Croatia

£1099


5.0 (2 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Tuscany

Cycling in Tuscany: Pisa to Florence

£1109


4.7 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : The Dolomites

Cross-country skiing in the Dolomites

£1109


4.7 (3 reviews)

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Winter snow holiday

7 nights,
single centre



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Italy : Campania

Coastal Cilento Walk

£1139


4.9 (9 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

Gems of the Amalfi Coast Walking

£1169


4.8 (5 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

£1189


4.6 (11 reviews)

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Self-guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Tuscany

Wine & Walk in Chianti

£1269


4.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Sardinia

Undiscovered Sardinia Cycling

£1389


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 : Sicily

Sicily: Vino & Volcanoes

£1449


5.0 (2 reviews)

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Cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

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Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

£1479


4.0 (1 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

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Italy : Italian Lakes

Cycling the Italian Lakes

£1859


4.9 (9 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

£2079


4.8 (13 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 : The Bay of Naples

Walking the Amalfi Coast

£1279


4.7 (12 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

£1559


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

£1679

 
 

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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

£2059


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.