Our self-guided Portugal activity holidays

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.

Where can I go on an activity holiday in Portugal?

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.

Algarve

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

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.

Madeira

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.

Azores

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.

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Why choose Headwater?


Walking the Waterways and villages of Madeira
Portugal: Madeira

Walking the Waterways and villages of Madeira

Perfect for year-round walking, the floating garden of Madeira is a paradise of tropical flowers, exotic birds and trees, romantic gorges and emerald seas. Staying in a luxury 5 star hotel and car hire provided ensures you see the best the island has to offer.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07MS
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £829per person, tour only

  • 5 Reviews
  • All accommodation
  • All buffet breakfasts and dinner on first night
  • Headwater navigation provided
Walking the Green Island of the Azores
Portugal: The Azores

Walking the Green Island of the Azores

São Miguel, the largest island in the archipelago has been called ‘The Green Island’ with its lush landscapes, rolling, verdant hillsides, candy-coloured hydrangeas and hot pink azaleas contrasting with the deep blue of the ocean.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07AS
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £929per person, tour only

  • 1 Reviews
  • All accommodation
  • All breakfasts and evening meals
  • Headwater navigation provided
Walking Rota Vicentina North Fishermen's Trail
Portugal: The Algarve

Walking Rota Vicentina North Fishermen's Trail

Rota Vicentina is spreading throughout the magnificent region of the Alentejo and Vicentine coast and the coastal trails are truly breathtaking.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08RT
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1239per person, tour only
  • All accommodation
  • All breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
Cycling in the Douro Valley
Portugal: Mainland Portugal

Cycling in the Douro Valley

Explore the Douro Valley and its historical villages. After a night in Porto, start cycling from the medieval village of Castelo Rodrigo, close to the Spanish border you'll ride through uniquely terraced vineyards on your way to port wine town of Peso da Regua.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07DV
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1419per person, tour only
  • All accommodation
  • All breakfasts and one evening meal.
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
Coimbra to Lisbon Cycling
Portugal: Mainland Portugal

Coimbra to Lisbon Cycling

Cycle from Coimbra, Portugal's old capital with UNESCO recognised heritage, along Portugal's Atlantic Coast through picturesque landscapes and charming villages, including Nazaré to Obidos a medieval walled town before spending the final three nights in Lisbon.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC11PO
  • Holiday typeSelf-guided cycling
  • Duration11 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1889per person, tour only
  • NEW FOR 2025  
  • All accommodation
  • All continental breakfasts and 1 evening meal
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
Marvels of Madeira Walk
Portugal: Madeira

Marvels of Madeira Walk

Perfect for year-round walking, the floating garden of Madeira is a paradise of tropical flowers, exotic birds and trees, romantic gorges and emerald seas. Luxury 4 and 5 star hotels throughout provide exquisite local cuisine with possibility of sampling the island's famous full-bodied wine.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07MF
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1219per person, tour only

  • 121 Reviews
  • All accommodation
  • All continental breakfasts, 2 picnics and 5 evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
Cycling in The Real Algarve
Portugal: The Algarve

Cycling in The Real Algarve

Discover a land that time forgot as you explore the unspoilt wild coastlines, pretty white villages and deserted cycling routes of the Algarve. The area is a birdwatchers paradise, with endemic and migratory species passing through from Africa and Northern Europe.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06AV
  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1279per person, tour only

  • 62 Reviews
  • All accommodation
  • All continental breakfasts and 5 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
Walk the Algarve's Wild West
Portugal: The Algarve

Walk the Algarve's Wild West

A walking discovery allowing you to see the best of the unspoilt Western Algarve region. The lush flora and diverse fauna of the Algarvian hinterland compliment the dramatic seascape scenery of the Atlantic coastline perfectly. Hotels are a brilliant mix of rustic charm and stylish grandeur, serving the best of local Portuguese cuisine.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW06AV
  • Holiday typeSelf-guided walking
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1049per person, tour only

  • 88 Reviews
  • All accommodation
  • All continental breakfasts and 3 evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
Porto Coastal Cycling
Portugal: Mainland Portugal

Porto Coastal Cycling

Varied beach-front cycling along some of the most spectacular stretches of coast we've ever seen! Starting in wine capital, Porto, your route heads south beach and bay-hopping to Aveiro, Portugal's Venice before finishing beside the beach at Praia de Mira.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07OP
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1449per person, tour only

  • 59 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
Walk the Garden Island of Madeira
Portugal: Madeira

Walk the Garden Island of Madeira

Based for 7 nights in Funchal in a choice of 3* or 5* accommodation, head out each day using public transport to explore this fascinating island, walking along levadas discovering the array of flora and fauna.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07ME
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £419per person, tour only

  • 4 Reviews
  • All accommodation
  • All breakfasts
  • Route notes provided
Walking the Green Coast of Minho
Portugal: Mainland Portugal

Walking the Green Coast of Minho

From your base in Viana do Castelo, one of the most beautiful cities in Northern Portugal, head out each day to walk along rivers, along the coast and in the nearby Serra de Arga mountain range.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07MH
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £449per person, tour only

  • 1 Reviews
  • All accommodation
  • All breakfasts
  • Route notes provided
Walking the Mountains, Valleys & Coast of Minho
Portugal: Mainland Portugal

Walking the Mountains, Valleys & Coast of Minho

Marked by the intense green of its fields and vineyards, the Minho regions' natural landscape is one of enormous beauty and biodiversity. Head from the mountains to the coast on this 7 night holiday.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07MV
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £679per person, tour only

  • 1 Reviews
  • All accommodation
  • All breakfasts
  • Route notes provided
  • Luggage transfers between hotels
Tour the Treasures of Portugal
Portugal: Mainland Portugal

Tour the Treasures of Portugal

Discover all that the incredible cities of Porto & Viana do Castelo have to offer, from local wine and port tastings to river cruises along the Douro, step into the real Northern Portugal.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeT07PO
  • Holiday typeIndependent tour
  • Duration7 nights, twin centre
  • Excellent for
  • From £1239per person, tour only

  • 2 Reviews
  • All accommodation
  • All breakfasts
Walk the Highlights of Northern Portugal
Portugal: Mainland Portugal

Walk the Highlights of Northern Portugal

Sample the world-class wine and local produce, discover an ancient castle, delightful forests, historical towns, and beautiful beaches overlooking the Atlantic Ocean as you meander across Northern Portugal.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08PO
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1269per person, tour only

  • 6 Reviews
  • All accommodation
  • All breakfasts and four packed lunches
  • Headwater navigation provided
  • Luggage transfers between hotels
Cycling the Algarve's Rota Vicentina
Portugal: The Algarve

Cycling the Algarve's Rota Vicentina

Follow the Rota Vicentina cycling path from Setubal to the Cape Sao Vicente, along rugged coastline with amazing views over cliffs and large sandy beaches.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07RV
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1289per person, tour only

  • 8 Reviews
  • All accommodation
  • All Breakfasts included
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
Portugal Coastal Way to Santiago
Portugal: Mainland Portugal

Portugal Coastal Way to Santiago

The Portuguese Camino de Santiago along the coast is one of the most unique and has been one of the main pilgrim routes to Santiago for centuries. Set out on a journey of discovery, not only of the country but of yourself as you follow in the footsteps of countless pilgrims and walkers.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW14CP
  • Holiday typePilgrimage
  • Duration14 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1309per person, tour only

  • 6 Reviews
  • All accommodation
  • All breakfasts
  • Route notes provided
  • Luggage transfers between hotels
Azores By E-bike
Portugal: The Azores

Azores By E-bike

In Terceira Island, explore the stunning coastline and the luxurious green pastures. Enjoy landscapes of dramatic lava coastline and natural pools, visit a volcano pit, a UNESCO World Heritage Town, and ride along lush green sceneries.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06AZ
  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1369per person, tour only

  • 4 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
Cycling in Portugal: From the Mountains to the Sea
Portugal: Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

You cycle through small villages and extensive vineyards, following the River Minho towards the Atlantic Ocean. The scenery is a stunning combination of high mountains, rolling river scenes, historic towns and dramatic coastal landscape.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07MI
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1429per person, tour only

  • 16 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
Walking the Algarve's South West
Portugal: The Algarve

Walking the Algarve's South West

Discover the South-West corner of the Algarve on our self-guided walk following coastal footpaths and inland trails.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW10AV
  • Holiday typeSelf-guided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1609per person, tour only

  • 32 Reviews
  • All accommodation
  • All continental breakfasts and 4 evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
Porto to Coimbra Cycling
Portugal: Mainland Portugal

Porto to Coimbra Cycling

Enjoy cycling from wine capital, Porto, south along the coast and bay-hopping to Aveiro, Portugal's Venice before heading inland and finishing in Coimbra, Portugal's old capital with UNESCO recognised heritage.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC09OP
  • Holiday typeSelf-guided cycling
  • Duration9 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1729per person, tour only

  • 57 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
Island Hopping in the Azores
Portugal: The Azores

Island Hopping in the Azores

Explore 5 of the 9 islands of the Azores archipelago, a scenically varied area to explore, with each island having its own characteristics, from steep craters to abundant wildlife and sites of historical interest. Internal flights or ferries included.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW14EC
  • Holiday typeSelf-guided walking
  • Duration14 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1819per person, tour only

  • 3 Reviews
  • All accommodation
  • All breakfasts and 5 evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
Porto to Lisbon Atlantic Ride
Portugal: Mainland Portugal

Porto to Lisbon Atlantic Ride

Follow scenic coastal routes along the Atlantic Coast of Portugal. This tour starts in Porto, with highlights including a scenic ride through the dunes of the Sao Jacinto Natural Reserve and an overnight in the picture-perfect fortified village of Obidos.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07PO
  • Holiday typeGuided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1545per person, tour only
  • All breakfasts, one wine tasting All accommodation Tour leader throughout Local bike hire Group arrival and departure transfers available
Walking in the Azores
Portugal: The Azores

Walking in the Azores

Guided trekking on Europe's undiscovered volcanic archipelago. Be it pocked with steep craters, a haven for wildlife or a place of historic interest, each of the nine islands is quite unique and ideally explored on foot. We visit the very best that four of these islands have to offer, walking through UNESCO vineyards, lava plateaux (or 'fajas') and sunken volcanoes.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07AZ
  • Holiday typeGuided walking
  • Duration7 nights, twin centre
  • Activity level
  • Excellent for
  • From £2299per person, tour only
  • All breakfasts and six lunches All accommodation Tour leader throughout All transport and listed activities Group arrival and departure transfers available
Portugal: Walking & Wine - Premium Adventure
Portugal: Mainland Portugal

Portugal: Walking & Wine - Premium Adventure

This 7-night guided walking holiday combines plentiful wine-tastings with relaxed walks through valleys and terraced vineyards, and alongside gushing rivers.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07OP
  • Holiday typeGuided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £2399per person, tour only

  • 2 Reviews
  • All breakfasts, two lunches, three dinners and three wine tastings All premium accommodation Tipping for all hotel staff, local staff and drivers Named tour leader, chosen for their expertise All transport and listed activities Group arrival and departure transfers available

Frequently asked questions

When is the best time to visit Portugal?

Split by the majestic Serra da Estrela mountains which are a natural divide between the humid Atlantic north and the dry Mediterranean south, Portugal has a relatively warm climate. Mild winters with rain and strong winds are followed by a lush spring, hot summer, and pleasant autumn.

This means that activity holidays in Portugal are possible for much of the year. However, summer may be better suited for beach relaxation than adventure activities, especially along the southern coastline where temperatures hover around 30°C.

The best month to go to Portugal for a walking or cycling holiday is May or September when the landscapes are lush, and the heat is not too extreme. In Madeira, there is a good chance of dry weather and pleasant temperatures from March to October, although spring is the best season for seeing it in all its floral majesty.

What should I wear for my activity holiday in Portugal?

Prioritise comfort when planning what to wear for your activity holiday in Portugal. You should also be prepared for mixed conditions no matter when you're travelling, in case weather is unsettled.

To keep you cool and dry throughout the day, opt for sweat-wicking sportswear in a breathable material. Bring a selection of T-shirts, shorts and longer leggings or trousers for a choice of coverage, and a sun hat and sunglasses to protect your face from harmful UV rays.

You should also carry a shirt or jumper for warmth and wind protection, and a waterproof jacket that you can use in the event of rain.

Sturdy walking boots are suitable but may be too hot in the summer, so look out for walking shoes that are lightweight and breathable for your Portugal activity holiday. If you're cycling, sports trainers with a good grip provide comfort and security.

What should I pack for my activity holiday in Portugal?

For a safe and enjoyable trip, include these must-haves when you pack for your activity holiday in Portugal:

  • Backpack – to carry your daily essentials including your route details, money and phone
  • Refillable water bottle
  • Camera
  • Walking poles – especially if you are tackling steep slopes and uneven terrain
  • First-aid kit – including insect repellent, sting relief cream, blister plasters, bandages, tweezers, antiseptic wipes and suncream

Why choose Portugal activity holidays with Headwater?

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:

  • Customer satisfaction: Check out our 5-star Feefo ratings from reviews given by our happy customers.
  • Expert knowledge: We have an intimate knowledge of destinations around the world thanks to our local experts in every location. They keep us up to speed with the best trails and things to do, so you can have an unmatched activity holiday.
  • Industry recognised: The British Travel Awards has consistently acclaimed us in categories such as Best Travel Company to Central Europe.
  • Trip protection: All our holidays are ABTA- and ATOL-protected so you can book with confidence.
  • Commitment to sustainability: We are always looking for ways to minimise the environmental impact of our holidays. Take a look at our People, Places & Planet plan that underpins our operations and our journey to becoming Nature Positive.

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