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A winter sun active holiday offers a perfect escape from the cold, gloomy weather of home, revitalizing both body and mind. With sunny skies and pleasant temperatures, you can enjoy outdoor activities like walking and cycling, which are often less tempting in our winter weather.

These holidays boost your mood, improve fitness, and provide a healthy dose of vitamin D. With destinations from the Canary Islands to Madeira, they offer stunning landscapes to explore while staying active.

A winter sun holiday is the perfect balance of relaxation and activity, recharging you for the year ahead.

 

Gozo

Walking on Glorious Gozo - Short Break

£459

NEW FOR 2025

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Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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Malta

Highlights of Secrets of Malta Walking

£489


4.0 (1 reviews)

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Self-guided walking

4 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Gozo

Walking on Glorious Gozo

£629

NEW FOR 2025

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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Malta

Discovering the Maltese Islands

£709


4.1 (7 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Walking the trails of Tenerife

£779

 
 

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Self-guided walking

7 nights,
single centre

Level: 2 & 3

Headwater
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Portugal : Madeira

Walking the Waterways and villages of Madeira

£899


4.0 (5 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Spain : The Canary Islands

Contrasts of Lanzarote

£939


5.0 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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Spain : The Canary Islands

Contrasts of La Gomera

£949


4.3 (4 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Walking on Gran Canaria

£989


5.0 (5 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Walking in Fuerteventura along the GR 131

£1039

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
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Spain : The Canary Islands

Volcanoes and Vineyards of Lanzarote

£1089


4.4 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 2+

Headwater
Navigation App

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Spain : The Canary Islands

Walking across La Gomera

£1239

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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Portugal : The Algarve

Walking Rota Vicentina North Fishermen's Trail

£1239

 
 

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Walking in Tenerife and La Palma

£1509

 
 

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Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
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Morocco

Highlights of Morocco - In Comfort

£1699

 
 

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Guided group walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Spain : The Canary Islands

Contrasts of Tenerife Walk (with transfers)

£1849

 
 

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Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
Navigation App

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Gozo

Walking on Gozo - Calypso's Isle

£749


4.6 (141 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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Spain : The Canary Islands

Contrasts of Tenerife Walk (with car hire)

£1169


4.7 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
Navigation App

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Portugal : Madeira

Marvels of Madeira Walk

£1219


4.7 (119 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Portugal : The Algarve

Cycling in The Real Algarve

£1279


4.7 (61 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Bermuda

Islands of Bermuda Walk

£1279


4.6 (34 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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Portugal : The Algarve

Walk the Algarve's Wild West

£1049


4.8 (86 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Gozo

Walking on Gozo - Calypso's Isle - Short Break

£489


4.8 (9 reviews)

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Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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Malta

Secrets of Malta Walking

£659


5.0 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Portugal : Madeira

Walk the Garden Island of Madeira

£719


4.7 (3 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Walking the Trails of La Palma

£899


4.3 (8 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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Spain : The Canary Islands

Walking in El Hierro

£969


5.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 2+

Headwater
Navigation App

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Spain : The Canary Islands

Highlights of El Hierro Walk

£1129


4.9 (10 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+ & 3

Headwater
Navigation App

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Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

£1289


4.9 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Spain : The Canary Islands

Walking in Gran Canaria and La Palma

£1439

 
 

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Self-guided walking

7 nights,
twin centre

Level: 1 to 2+

Headwater
Navigation App

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Cape Verde

Cape Verde's Northern Islands - With Private Guide

£1599


4.8 (4 reviews)

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Private guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Portugal : The Algarve

Walking the Algarve's South West

£1609


4.8 (32 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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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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