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Showing 24 out of 337 trips

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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Portugal : The Azores

Walking the Green Island of the Azores

£929


5.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

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
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Portugal : Mainland Portugal

Cycling in the Douro Valley

£1419

 
 

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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

£1889

NEW FOR 2025

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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
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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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Portugal : Mainland Portugal

Porto Coastal Cycling

£1449


4.4 (59 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Portugal : Mainland Portugal

Walking the Green Coast of Minho

£449


4.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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Portugal : Mainland Portugal

Walking the Mountains, Valleys & Coast of Minho

£679


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

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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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Portugal : Mainland Portugal

Tour the Treasures of Portugal

£1099


4.5 (2 reviews)

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Self-guided cultural tour

7 nights,
twin centre

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Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

£1269


4.5 (6 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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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Portugal : Mainland Portugal

Portugal Coastal Way to Santiago

£1309


5.0 (6 reviews)

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Self-guided pilgrimage

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Portugal : The Azores

Azores By E-bike

£1369


4.0 (4 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
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Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

£1429


4.5 (16 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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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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Portugal : Mainland Portugal

Porto to Coimbra Cycling

£1729


4.8 (56 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Portugal : The Azores

Island Hopping in the Azores

£1819


4.3 (3 reviews)

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Self-guided walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Portugal : Mainland Portugal

Porto to Lisbon Atlantic Ride

£1745

 
 

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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

£2299

 
 

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Guided group walking

7 nights,
twin centre

Level: 3
Stretching

Printed route
directions

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Portugal : Mainland Portugal

Portugal: Walking & Wine - Premium Adventure

£2399


4.5 (2 reviews)

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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.