Who doesn't enjoy a winter escape?

The temperatures may be dipping, but this doesn’t mean you can’t look forward to a wonderful self-guided holiday with Headwater. Our winter snow holidays take you cross-country skiing in Norway and snowshoeing in Finland, while our winter sun trips allow you to soak up the pleasant temperatures and idyllic coastal landscapes in the south Mediterranean countries of Malta, Portugal, Spain and many more.

Whatever your idea of a winter wonderland, our collection offers something for everyone. Take a look at our winter holidays below to find out more.

 

Malta + Gozo

Highlights of Secrets of Malta Walking

£609


4.5 (2 reviews)

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Self-guided walking

4 nights,
single centre

Level: 2
Moderate

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Malta + Gozo

Discovering the Maltese Islands

£839


4.1 (7 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

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Spain : The Canary Islands

Walking the trails of Tenerife

£879


4.5 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2 & 3

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Spain : The Canary Islands

Contrasts of Lanzarote

£1039


5.0 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

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Spain : The Canary Islands

Contrasts of La Gomera

£1049


4.2 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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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

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Spain : The Canary Islands

Walking on Gran Canaria

£1089


5.0 (7 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

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Spain : The Canary Islands

Volcanoes and Vineyards of Lanzarote

£1189


4.4 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 2+

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Malta + Gozo : Malta

Walking on Gozo - Calypso's Isle

£869


4.6 (143 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

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Spain : The Canary Islands

Contrasts of Tenerife Walk (with car hire)

£1269


4.7 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

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Italy : The Bay of Naples

Paths of the Amalfi Coast

£829


4.6 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

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Bermuda

Islands of Bermuda Walk

£1409


4.6 (37 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1
Leisurely

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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

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Portugal : Madeira

Marvels of Madeira Walk

£1429


4.7 (124 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Portugal : The Algarve

Walk the Algarve's Wild West

£1179


4.8 (89 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Norway : Gudbrandsdalen

Cross-country skiing at Venabu

£1919


4.8 (293 reviews)

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Winter snow holiday

7 nights,
single centre



Spain

Hidden Valleys of Cordoba Walk

£569


4.8 (53 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

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Cyprus

Walking the Akamas Peninsula

£759


4.5 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1 & 2

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Malta + Gozo : Malta

Secrets of Malta Walking

£789


5.0 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

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Cyprus

Contrasts of Cyprus Walking

£859


4.6 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+ to 2+

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Switzerland : The Bernese Oberland

Cross country skiing in Kandersteg - Short Break

£919


4.8 (4 reviews)

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Winter snow holiday

5 nights,
single centre



Austria : The Tyrol

Self guided cross-country skiing at Leutasch

£1039


4.5 (13 reviews)

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Winter snow holiday

7 nights,
single centre

Printed route
directions

Switzerland : The Bernese Oberland

Cross country skiing in Kandersteg

£1169


4.7 (6 reviews)

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Winter snow holiday

7 nights,
single centre



Spain : The Canary Islands

Highlights of El Hierro Walk

£1229


4.9 (11 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+ & 3

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Finland

Cross-country skiing in Lapland

£1249


4.8 (24 reviews)

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Winter snow holiday

7 nights,
single centre



Spain : The Canary Islands

Walking in El Hierro

£1299


4.5 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 2+

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Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

£1459


4.9 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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Cape Verde

Cape Verde's Northern Islands - With Private Guide

£1699


4.9 (7 reviews)

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Private guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Portugal : The Algarve

Walking the Algarve's South West

£1789


4.8 (32 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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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

China

Walking the Charms of China - With Private Guide

£3349

 
 

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Private guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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

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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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