Seeking a coastal escape that goes beyond a beach break? Look no further than our Portugal activity holidays.
The natural splendour of this diverse destination makes it a dream to explore on foot or by bike. Pace or pedal through lush countryside and along golden sands or climb craggy mountains to spectacular viewpoints. Off the mainland, the mysterious volcanic lakes and basalt beaches of the Azores await, as well as the breathtaking mountain scenery and exotic flora of Madeira.
Portugal's culture is just as rich and diverse as its landscapes, so there's no shortage of extraordinary experiences for you to enjoy. The country's seafaring past is evidenced by port cities alive with colourful cuisine and magnificent Baroque buildings. Elsewhere, awe-inspiring architectural sites highlight how the Romans and Moors shaped the nation's early identity.
Our self-guided Portugal activity holidays give you the freedom to travel at your own pace while our detailed route descriptions, maps and GPS-powered Headwater Navigation app keep you on track. Slowing down gives you the chance to take in the scenery and while away time at a series of secret viewpoints.
We rate most of our Portugal tours at a moderate activity level, but there's also the option of leisurely routes with gentle slopes or more challenging climbs where hikers and bikers are rewarded with spectacular views.
Discover details of our Portugal activity holidays below and start planning your next adventure.
We have a wide choice of places for you to go on your activity holiday in Portugal, whether you want to walk rural interior paths, stroll lively cities, cycle the coastline or indulge in sea-based sports. The key to finding the right holiday is to decide on your preferred scenery, difficulty and mode of transport. Remember, we're always here to help with recommendations too.
Look at our best destinations for Portugal activity holidays and select your perfect match.
Portugal's southern coastal region is a land of contrasts. Wide sandy beaches with modern resorts neighbour fishing villages on small bays, while lush alpine-like meadows await just a little way inland. In between you'll find lively towns with excellent dining options.
You can spend a week walking along the coastline with our The Algarve from West to East tour. Or you can hike down to the region's wild western corner, travelling from the village of Carrapateira and along the Rota Vicentina all the way to Cabo de Sao Vicente, the farthest-flung corner of Europe.
Porto, Portugal's second-largest city, is an extraordinary place, overflowing with colour and culinary delights. Its historic centre is a UNESCO World Heritage Site and its many cultural and architectural gems overlook the Douro river.
The surrounding countryside ranges from riverside vineyards by the Douro, where port wine is crafted, to coastal lagoons beloved by vibrant birds such as pink flamingos and turquoise kingfishers.
Try our Porto Coastal Cycling tour to uncover the best of this characterful corner of Portugal.
Predominantly dry from late spring through summer with mild winters and warm summers, Madeira is an excellent year-round destination for a Portugal activity holiday.
Known as the Floating Garden, this island off the northwest coast of Africa is incredibly lush with diverse flora and exotic animals. The island is best discovered on hikes through the central mountains, although the view of the azure ocean from the coastal cliffs is captivating.
Nine islands make up the Azores archipelago which enjoys an enviable mid-Atlantic position. Each island has its own character and combination of mesmerising landscapes, ranging from mirror-like mountain lakes, thermal pools and black sand bays to fairytale farms and woodland.
The largest island, São Miguel, has a surreal vibrancy with bright green fields, hot pink flowers and a deep blue ocean. Especially in spring and summer, our Walking the Green Island of the Azores itinerary is sure to leave a lasting impression.
Self-guided walking
7 nights,
single centre
Level: 2
Moderate
Headwater
Navigation App
10% OFF THIS TRIP
VIEW TRIPSelf-guided walking
7 nights,
single centre
Level: 2+
Moderate plus
Headwater
Navigation App
20% OFF THIS TRIP
VIEW TRIPSelf-guided walking
8 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
10% OFF THIS TRIP
VIEW TRIPSelf-guided cycling
7 nights,
hotel-to-hotel
Level: 3
Stretching
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIPSelf-guided cycling
11 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIPSelf-guided cycling
6 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIPSelf-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIPSelf-guided walking
6 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIPSelf-guided cycling
7 nights,
hotel-to-hotel
Level: 1
Leisurely
Headwater
Navigation App
10% OFF THIS TRIP
VIEW TRIPSelf-guided walking
7 nights,
single centre
Level: 2
Moderate
Headwater
Navigation App
20% OFF THIS TRIP
VIEW TRIPSelf-guided walking
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
10% OFF THIS TRIP
VIEW TRIPSelf-guided walking
7 nights,
single centre
Level: 2
Moderate
Headwater
Navigation App
20% OFF THIS TRIP
VIEW TRIPSelf-guided pilgrimage
9 nights,
hotel-to-hotel
Level: 2
Moderate
Printed route
directions
5% OFF THIS TRIP
VIEW TRIPSelf-guided pilgrimage
13 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
5% OFF THIS TRIP
VIEW TRIPSelf-guided pilgrimage
13 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
5% OFF THIS TRIP
VIEW TRIPSelf-guided walking
14 nights,
hotel-to-hotel
Level: 2
Moderate
Printed route
directions
15% OFF THIS TRIP
VIEW TRIPSelf-guided cycling
7 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Headwater
Navigation App
20% OFF THIS TRIP
VIEW TRIPSelf-guided walking
8 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Headwater
Navigation App
20% OFF THIS TRIP
VIEW TRIPSelf-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIPSelf-guided walking
10 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
10% OFF THIS TRIP
VIEW TRIPSelf-guided cycling
9 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIPSelf-guided walking
14 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIPGuided group cycling
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.
With nearly 40 years' experience curating walking and cycling trips, you can be confident in our Portugal activity holidays. We are committed to providing each Headwater traveller with great service and an amazing experience. Here's how you know we're a company you can trust: