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Rethink Your Stay

Showing 38 out of 323 trips

Go beyond the ordinary on your next holiday. Headwater have been researching and sourcing the finest, friendliest and most charming hotels for 33 years, staying in historic properties which unlock the local traditions that reach back through the generations and make the past come alive in front of your eyes.

You can expect a royal welcome in the Loire Valley, where you'll not be a visitor but a guest at one of the many famous white-walled chateaux that define the region, staying in very own 16th-century castle where both King Charles VII and Louis XI have slept.

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Portugal : Madeira

Walking the Waterways and villages of Madeira

£1079


4.2 (6 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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Italy : Puglia

Journey through Puglia to Matera

£1149


4.9 (14 reviews)

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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Norway

Cycling in the Lofoten Islands

£3839


5.0 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

FREE CASE OF WINE WITH BOOKING

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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

FREE CASE OF WINE WITH BOOKING

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Italy : Veneto

Walking in the Venetian Hills

£1089


4.7 (90 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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Italy : Puglia

Self Guided Walking in Puglia: From Lecce to Matera

£1169


4.7 (65 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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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

FREE CASE OF WINE WITH BOOKING

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Italy : Tuscany

A Taste of Tuscany Cycling

£1319


4.9 (28 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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Portugal : The Algarve

Cycling in The Real Algarve

£1399


4.7 (66 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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Switzerland : Valais

Walking in Val D'Anniviers

£1649


4.5 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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Spain : Catalonia

Catalan Classic Walk

£989


4.7 (79 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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France : The Dordogne

Dordogne River Walk

£1249


4.7 (32 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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Italy : Puglia

Contrasts of Puglia Cycling

£1449


4.6 (125 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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United Kingdom : The Cotswolds

Best of the Cotswolds Walk

£1779


4.7 (15 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

FREE CASE OF WINE WITH BOOKING

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Italy : Piedmont

Gastronomic Barolo Walk

£1829


4.9 (97 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

£859

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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France : Burgundy

Cycling The Grand Crus of Burgundy

£1249


5.0 (1 reviews)

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Self-guided cycling

6 nights,
twin centre

Level: 1+
Leisurely plus

Printed route
directions

FREE CASE OF WINE WITH BOOKING

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Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

£1259

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

FREE CASE OF WINE WITH BOOKING

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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

FREE CASE OF WINE WITH BOOKING

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Spain : Extremadura

Cycling Central Spain in Style

£1489

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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Greece : Crete

Walking the Wonders of Crete

£1539

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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Italy : Emilia Romagna

Emilia Romagna: Bologna to Parma Cycling

£1659


4.7 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

FREE CASE OF WINE WITH BOOKING

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France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

£1719


4.8 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

FREE CASE OF WINE WITH BOOKING

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Portugal : Mainland Portugal

Porto to Coimbra Cycling

£1829


4.8 (56 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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Slovenia

Secrets of Slovenia Cycling

£1849


4.9 (14 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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Morocco

Morocco: Mountains, Desert & Coast

£2019

NEW FOR 2025

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Self-guided cultural tour

7 nights,
hotel-to-hotel



FREE CASE OF WINE WITH BOOKING

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Canada : Sunshine Coast

Walking Canada's Sunshine Coast

£2609


4.7 (3 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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USA : Maine

Cycling Maine's Coast & National Park

£3199

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

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Japan

Shikoku Pilgrimage Trail

£3329


5.0 (1 reviews)

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Self-guided pilgrimage

10 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

FREE CASE OF WINE WITH BOOKING

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Japan

Walk the Kumano Kodo

£3359


5.0 (4 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

FREE CASE OF WINE WITH BOOKING

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Japan

Walk the Nakasendo Trail

£3399

 
 

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

FREE CASE OF WINE WITH BOOKING

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Japan

Exploring the land of Shogun and Samurai

£3879

NEW FOR 2025

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Self-guided cultural tour

10 nights,
hotel-to-hotel



FREE CASE OF WINE WITH BOOKING

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Morocco

Atlas Panorama

£649

 
 

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Albania

Highlights of Albania

£1219

 
 

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Guided group walking

9 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Egypt

Ancient Egypt & Nile Cruise

£1399

 
 

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Guided group walking

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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Peru

The Inca Trail in Comfort

£2599

 
 

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

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Peru

Peru Explorer

£4699

 
 

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Guided group walking

19 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Kenya

Kenya Photographic Safari with Paul Goldstein - Premium Adventure

£7199

 
 

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Guided group walking

6 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.