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Showing 70 out of 341 trips

Spain : The Canary Islands

Walk the Bonita Island of La Palma

£879

NEW FOR 2026

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Self-guided walking

7 nights,
single centre

Level: 2+ & 3

Headwater
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Spain : Asturias

Majestic Mountains of the Picos de Europa

£989


4.7 (11 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 3

Navigation App

15% OFF THIS TRIP

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Spain : Andalucia

Walking in Sierra de Aracena

£989


4.8 (16 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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Spain : The Canary Islands

Contrasts of Lanzarote

£1019


5.0 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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Portugal : The Azores

Walking the Green Island of the Azores

£1029


5.0 (3 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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Spain : The Canary Islands

Walking the trails of Tenerife

£1059


4.6 (5 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2 & 3

Headwater
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Spain : The Canary Islands

Walking in Fuerteventura along the GR 131

£1139


4.8 (4 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
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Portugal : Madeira

Walking the Waterways and villages of Madeira

£1139


4.2 (6 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
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Portugal : The Algarve

Walking Rota Vicentina North Fishermen's Trail

£1209


4.5 (2 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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10% OFF THIS TRIP

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Spain : The Canary Islands

Contrasts of La Gomera

£1229


4.2 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Spain : The Canary Islands

Walking on Gran Canaria

£1249


5.0 (7 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
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Spain : The Canary Islands

Volcanoes and Vineyards of Lanzarote

£1259


4.4 (8 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 2+

Headwater
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Spain : The Canary Islands

Walking across La Gomera

£1349

NEW FOR 2026

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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20% OFF THIS TRIP

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Spain : Galicia

Cycle from Tui to Santiago in Style: Stay in Historic Paradors Hotels

£1439

NEW FOR 2026

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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15% OFF THIS TRIP

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Portugal : Mainland Portugal

Cycling in the Douro Valley

£1589

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
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Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

£2049

 
 

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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15% OFF THIS TRIP

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Spain : The Canary Islands

Contrasts of Tenerife Walk (with transfers)

£2169

 
 

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Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
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Spain : The Canary Islands

Contrasts of Tenerife Walk (with car hire)

£1429


4.8 (12 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
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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
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15% OFF THIS TRIP

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Portugal : Madeira

Marvels of Madeira Walk

£1469


4.7 (129 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Spain : Catalonia

Catalan Classic Walk

£1129


4.7 (79 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Portugal : The Algarve

Walk the Algarve's Wild West

£1169


4.8 (90 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Spain : Balearic Islands

Cycling in Mallorca: Coast to Coast

£1299


4.7 (35 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Spain : Catalonia

Contrasts of Catalunya Cycling

£1419


4.7 (56 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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Spain : Andalucia

White Villages of Andalucia Walk

£1489


4.9 (139 reviews)

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Guided group walking

7 nights,
single centre

Level: 1+
Leisurely plus

15% OFF THIS TRIP

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Spain : Andalucia

Cycling in Andalucia: Seville to Cadiz

£1499


4.4 (17 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
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Portugal : Mainland Portugal

Porto Coastal Cycling

£1639


4.4 (59 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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10% OFF THIS TRIP

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Spain : Finisterre Camino Way

Camino Finisterre: Santiago de Compostela to Finisterre

£459

NEW FOR 2026

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Self-guided pilgrimage

5 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

5% OFF THIS TRIP

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Portugal : Mainland Portugal

Walking the Green Coast of Minho

£649


4.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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Spain : French Camino

Camino Frances: Stage 2 - Logrono to Burgos

£679

NEW FOR 2026

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Self-guided pilgrimage

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

5% OFF THIS TRIP

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Spain : Catalonia

Catalan Classic Walk - Short Break

£679


4.7 (7 reviews)

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Spain : North Camino Way

Camino Ingles: Ferrol to Santiago de Compostela

£759

NEW FOR 2026

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Self-guided pilgrimage

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

5% OFF THIS TRIP

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Spain : French Camino

Camino Frances: Stage 5 - Sarria to Santiago de Compostela

£789

NEW FOR 2026

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Self-guided pilgrimage

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

5% OFF THIS TRIP

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Portugal : Mainland Portugal

Walking the Mountains, Valleys & Coast of Minho

£789


5.0 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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10% OFF THIS TRIP

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Spain

Walking Mallorca's Mountains and Coast

£829


4.5 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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10% OFF THIS TRIP

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Spain / France

Camino Norte: Special - Hendaye to Bilbao

£859

NEW FOR 2026

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Self-guided pilgrimage

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

5% OFF THIS TRIP

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Spain : Andalucia

Walking the White Villages of the Alpujarras

£859


4.6 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
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10% OFF THIS TRIP

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Spain : Balearic Islands

Walking the Coastal Trails of Menorca

£909


4.6 (60 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1
Leisurely

Headwater
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10% OFF THIS TRIP

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Spain : French Camino

Camino Frances: Stage 3 - Burgos to Leon

£959

NEW FOR 2026

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Self-guided pilgrimage

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

5% OFF THIS TRIP

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Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

£969


4.8 (8 reviews)

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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10% OFF THIS TRIP

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Portugal : Madeira

Walk the Garden Island of Madeira

£979


4.8 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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Portugal / Spain

Camino Portugues: Central way from Lima to Santiago de Compostela

£1069

NEW FOR 2026

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Self-guided pilgrimage

9 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

5% OFF THIS TRIP

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Spain / France

Camino Frances: Stage 1 - Saint-Jean-Pied-de-Port to Logrono

£1119

NEW FOR 2026

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Self-guided pilgrimage

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

5% OFF THIS TRIP

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Spain : French Camino

Camino Frances: Stage 4 - Leon to Sarria

£1139

NEW FOR 2026

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Self-guided pilgrimage

11 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

5% OFF THIS TRIP

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Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

£1179

 
 

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

10% OFF THIS TRIP

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Spain : The Canary Islands

Walking in El Hierro

£1209


4.5 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 2+

Headwater
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10% OFF THIS TRIP

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Portugal / Spain

Camino Portugues: Coastal way from Porto to Santiago de Compostela

£1229

NEW FOR 2026

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Self-guided pilgrimage

13 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

5% OFF THIS TRIP

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Spain : Galicia

Highlights of the Camino de Santiago Walk

£1229


4.8 (19 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Headwater
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15% OFF THIS TRIP

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Portugal : Mainland Portugal

Tour the Treasures of Portugal

£1279


4.8 (5 reviews)

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Cultural tour

7 nights,
twin centre

7 meals
included

10% OFF THIS TRIP

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Spain : Valencia

Cycling Valencia and the Orange Blossom Coast

£1299


4.6 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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15% OFF THIS TRIP

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Spain : Catalonia

Classic Catalan Cycling

£1309


4.8 (12 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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15% OFF THIS TRIP

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Spain : Andalucia

Three Cities of Andalucia

£1359


4.8 (6 reviews)

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Cultural tour

7 nights,
hotel-to-hotel

7 meals
included

10% OFF THIS TRIP

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Spain : Pilgrimage Primitivo

Camino Primitivo: Stage 1 - Oviedo to Santiago de Compostela

£1409

NEW FOR 2026

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Self-guided pilgrimage

15 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

5% OFF THIS TRIP

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Spain : Rioja

Vineyards of La Rioja Cycling

£1419


4.5 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

10% OFF THIS TRIP

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Portugal / Spain

Camino Portugues: Central way from Porto to Santiago de Compostela

£1449

NEW FOR 2026

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Self-guided pilgrimage

13 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

5% OFF THIS TRIP

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Spain : The Canary Islands

Highlights of El Hierro Walk

£1479


4.9 (11 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+ & 3

Headwater
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20% OFF THIS TRIP

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Spain : Extremadura

Cycling Central Spain in Style

£1519


4.5 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

15% OFF THIS TRIP

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Portugal / Spain

Portugal Coastal Way to Santiago

£1539


5.0 (11 reviews)

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Self-guided walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

15% OFF THIS TRIP

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Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

£1569


4.9 (10 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

20% OFF THIS TRIP

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Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

£1579


4.5 (6 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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20% OFF THIS TRIP

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Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

£1639


4.5 (17 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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15% OFF THIS TRIP

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Portugal : The Algarve

Walking the Algarve's South West

£1719


4.9 (34 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

10% OFF THIS TRIP

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Spain : French Camino

Camino Frances: Stage 4 and 5 - Leon to Santiago de Compostela

£1799

NEW FOR 2026

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Self-guided pilgrimage

17 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

5% OFF THIS TRIP

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Portugal : Mainland Portugal

Porto to Coimbra Cycling

£1889


4.8 (56 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

15% OFF THIS TRIP

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Portugal

Island Hopping in the Azores

£2079


4.6 (5 reviews)

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Self-guided walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

15% OFF THIS TRIP

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Spain

Camino Frances

£4509

 
 

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Self-guided pilgrimage

42 nights,
hotel-to-hotel

Level: 2 & 2+

Printed route
directions

5% OFF THIS TRIP

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Spain : Mallorca

Walking in Mallorca

£1599


5.0 (6 reviews)

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Guided group walking

7 nights,
twin centre

Level: 2
Moderate

Printed route
directions

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Portugal : Mainland Portugal

Porto to Lisbon Atlantic Ride

£1635

 
 

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Guided group cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Portugal : The Azores

Walking in the Azores

£2519

 
 

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Guided group walking

7 nights,
twin centre

Level: 3
Stretching

Printed route
directions

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Spain : Catalonia

Cycling the Mediterranean Coast in Spain

£2849

 
 

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Guided group cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

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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.