Rethink Your Stay

Showing 40 out of 328 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

£1059


4.2 (6 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
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Italy : Puglia

Journey through Puglia to Matera

£1149


4.8 (11 reviews)

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Headwater
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Norway

Cycling in the Lofoten Islands

£3569


5.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Italy : Veneto

Heart of Veneto Cycling

£1039


4.8 (72 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
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Italy : Veneto

Walking in the Venetian Hills

£1089


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

£1169


4.7 (55 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

£1269


4.9 (29 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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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
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France : Provence

Cotes du Ventoux Cycling

£1389


4.8 (36 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Portugal : The Algarve

Cycling in The Real Algarve

£1419


4.7 (64 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Switzerland : Davos

Walking in Val D'Anniviers

£1649


5.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Printed route
directions

Spain : Catalonia

Catalan Classic Walk

£989


4.7 (78 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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France : The Dordogne

Dordogne River Walk

£1199


4.7 (29 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : Puglia

Contrasts of Puglia Cycling

£1469


4.6 (124 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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United Kingdom : The Cotswolds

Best of the Cotswolds Walk

£1749


4.8 (13 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

Italy : Piedmont

Gastronomic Barolo Walk

£1809


4.9 (93 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

£819

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
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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

Norway

Cross Country Skiing at Rondane National Park

£1399

NEW FOR 2025

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Winter snow holiday

5 nights,
single centre



Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

£1409

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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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
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Italy : Sardinia

Undiscovered Sardinia Cycling

£1549


4.7 (19 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Italy : Emilia Romagna

Emilia Romagna: Bologna to Parma Cycling

£1579


4.7 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

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France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

£1719


4.8 (4 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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France : Provence

Provence Velo Vin Voyage

£1729


4.0 (1 reviews)

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Self-guided cultural tour

7 nights,
hotel-to-hotel



Slovenia

Secrets of Slovenia Cycling

£1799


4.9 (12 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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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
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Morocco

Morocco: Mountains, Desert & Coast

£2179

NEW FOR 2025

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Self-guided cultural tour

7 nights,
hotel-to-hotel



Canada : Prince Edward Island

Walking Canada's Sunshine Coast

£2549


4.7 (3 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
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USA : Maine

Cycling Maine's Coast & National Park

£3119

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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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

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

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

Japan

Japan: Hiroshima & Island Hopping

£3499

NEW FOR 2025

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Multi-activity holiday

10 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Morocco

Atlas Panorama

£699

 
 

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Albania

Highlights of Albania

£949

 
 

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Guided group walking

9 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Egypt

Ancient Egypt & Nile Cruise

£1499

 
 

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Guided group walking

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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

Peru

Peru Explorer

£4699

 
 

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Guided group walking

19 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Kenya

Kenya Photographic Safari with Paul Goldstein - Premium Adventure

£6549

 
 

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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.