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This self-drive trip sweeps down the country from north to south, starting in Porto and in the vineyards of Portugal's finest wine-producing area, the Douro. Then drive through the enchanting forests and palaces of central Portugal to the south for some hiking among the Alentejo's cork oaks. After a stay on the Costa Vicentina, one of the loveliest stretches of coastline anywhere for our money, finish in ever-changing Lisbon.
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Settle into your hotel, in the pretty heart of the old city. It's a short walk down to the Ribeira district, where you can wander along the waterside, watching the rabelos (small wooden boats) bob on the river’s currents. There are plenty of spots to have a drink and watch the sun go down over the river, with views across to Vila Nova de Gaia.
Your private guide will come to your hotel this morning to take you on a full day's exploration, discovering the hidden corners of this enchanting city. Spend the morning exploring the Cathedral and admiring the famous blue tiles on display at the São Bento train station. After a tasty lunch, cross the river to visit one of our favourite wine lodges in Vila Nova de Gaia.
Pick up your car to travel east into the heart of the Douro, perhaps stopping en route to wander through the historic town of Guimaraes. The Casa de Mateus is also nearby, before you arrive in the most famous, and arguably prettiest, wine producing area in Portugal. Here you stay in a beautiful quinta, perched up in the hills above the River Douro.
Enjoy a small boat cruise along the Douro past sloping river banks blanketed with vineyards and dotted with charming white quintas. Along the way, your captain will regale you with stories and history of the region that he knows so well, before taking you to his family’s historic quinta, one of the valley’s oldest. The family proudly produces wine using the most traditional methods, which you can enjoy for lunch along with ingredients sourced from here on the farm.
Relax at your wonderful hotel today, taking the time to hike around the property, enjoying the views over the Douro river. Visit the winery and taste the wines, or head up to one of the tiny hamlets for a couple of hours' walk through the vineyards back down to Pinhão. You might also like to go for lunch at the stunning location of the DOC Restaurant by chef Rui Paula. There are few places where you can enjoy this calibre of food in such an idyllic setting.
From the Douro travel south to your stunning Palace hotel in the forest of Bussaco where you can explore the forest and garden surrounding your hotel, the National Forest of Buçaco, created and protected by the Carmelite Monks that settled in this area in the 16th Century. The area is full of pathways and little chapels hidden in the lush forest and you can choose the length and height gain of your walk. From the highest point, the Cruz Alta, you can enjoy wonderful views over the surrounding plains, before a fine dinner in the terrace of the beautiful Neo-Manueline style palace that hosts you tonight.
Your route today takes you right past the city of Coimbra, a cradle of Portugal's famous Fado music, and home to one of the oldest universities in Europe, full of unique, intriguing chapels and libraries. Continue southeast later, headed towards the Spanish border, and the hilltop village of Marvão. One of the most impressive settings in Portugal, the village naturally has commanding views over the plains for miles around. Watch the sunset from one of the viewing platforms or the castle, before heading to one of our recommended restaurants for dinner.
Perched on a ridge overlooking the Tejo river valley, Marvão has been a site of strategic importance from the earliest times, something you can fully understand when you climb the ancient cobbled path and enter the castle to discover the vast views around you. Today we suggest you take a hike to appreciate the full scale of the place. With a short transfer to the tiny village of Galegos, right in the border with Spain, you can hike 12km back to Marvão along ancient paths surrounded by giant cork oak fields. The views of the hilltop village guide your way on this, one of our absolute favourite hikes among the landscapes of Southern Portugal.
It's only a couple of hours to Évora, so you might like to linger in Marvão, or head out on another hike before departure. If you don't want to head straight to Alentejo's capital, it's well worth diverting to another stunningly located village, Monsaraz, a short drive to the east. The views over the Alqueva reservoir from the fortress are superb. Continue later to enter the compact city of Évora, where your charming hotel is located just inside the historic city wall, in the shade of the aqueduct.
Spend the day with your guide exploring Évora and the surrounding Iron Age monuments. The town is most famous for its striking Roman temple, one of the finest Roman remains on the Iberian Peninsula. There is also the Capela dos Ossos – a chapel lined with the bones and skulls of thousands of townspeople. A short way outside the town is the Cromeleque dos Almendres, a peaceful and pretty site of over 100 granite monoliths, a perfect place to learn about the importance of cork as a crop in this part of the world, home to 60% of the world's cork production.
Drive to the coast today, perhaps dropping your bags before heading off on a strikingly beautiful cliff-top path established by the fishermen. You can start walking from the Cabo Sardão Lighthouse to follow the coastal path of the Rota Vicentina. Relax at your very comfortable hotel this evening, a rural estate with pretty cottages and a lovely pool. Your dinners are included here, and your delightful hosts will make sure you're well fed with some of the best of the local produce.
Today's suggested walk begins with one of the most outstanding views in the entire territory: Odeceixe beach seen from the majestic Ponta em Branco. As well as Odeceixe, the 12km route passes any number of beautiful beaches: Alteirinhos, Carvalhal, Machados and Amália. In Azenha do Mar you will find a natural fishing harbour where you can rest and refresh your toes in the chilly Atlantic waters. The walk finishes at the welcoming village of Zambujeira do Mar, where you can enjoy a drink before calling the hotel for a short ride back to your comfortable retreat, or continue on foot if you're feeling energetic.
Your last day here is free to be as active or relaxed as you like. You could easily follow the coastal trail further north towards Milfontes, while a short drive south takes you to the small village of Aljezur, an attractive Moorish village noted for its 10th Century castle. For a more relaxed day you could enjoy the pool and lounge at your hotel, or stroll directly down to the beach. Of course, there are no shortage of lovely beaches within easy reach, you might even have one to yourself!
Head to Lisbon, perhaps via the Setúbal Peninsula, home to the Arrábida Natural Park. The Mediterranean pine forests and chalk cliffs here have a variety of trails to explore, with glorious views from the top over the ocean and towards Lisbon. Down on the water you can kayak or take a boat trip to spot dolphins, or simply relax on golden sands and take a dip in the startlingly clear waters. Drop off your hire car before settling into your Lisbon hotel later. This characterful bolthole is nestled up against the Castelo de São Jorge, Lisbon's iconic castle, which sits perched up above the city's red-roofed skyline.
Your guide collects you this morning for your walking tour of the Portuguese capital. The barrios of Lisbon are as intriguing as they are diverse, from the labyrinthine alleyways of Alfama to the chic boutiques and galleries of Baixo and Chiado. This afternoon is yours to discover more of Lisbon, with its quirky, historic shops and striking churches. This evening you might like to participate in a cherished Portuguese tradition: a fado show with dinner. Our favourite spot in the heart of Alfama is a great place to experience the strains of a traditional 12-stringed guitar and the sultry voices of the city’s best 'fadistas'.
Time to hand in the keys to the car and head home today. Having whizzed through Portugal in the digital space, hopefully you're sufficiently intrigued to take the journey for real. To make that happen, you'll find various ways to get in touch below or you can request a PDF of the full itinerary with more details should you prefer.
Note: This is just an itinerary idea and we'll therefore tailor everything to you.
If the idea of switching between historic cities, hilltop villages, sweeping wine valleys, silent cork oak forests and the golden beaches of the Atlantic sounds like your idea of a good holiday, then it probably is for you. If you’re confident behind the wheel of a car, then that's a green light to get excited isn't it?
In terms of physical exertion on this trip, it is defined entirely by you. Many of the places featured in this holiday are best enjoyed on foot, be it exploring the steep cobbled alleyways of Alfama in Lisbon, descending through the vineyards of the Douro, or hiking up to hilltop villages through the cork oak trees near the Spanish border. In the more rural areas, horse riding is a possibility, as is mountain biking. Down on the coast, you have the ocean, so lots of opportunity for swimming, kayaking, surfing and paddle boarding should that appeal.
Want something more focused on walking? Take a look at our 8-day Alentejo Inn to Inn walking tour.
There’s an awful lot of flexibility built into this trip, so often it’s a case of understanding what you like to do and pointing you in the right direction or making a new suggestion. Granted though you might not have two weeks, so just let us know how long you want to go for and we’ll give you some ideas. This can take the form of trimming it down to a week or 10 days, but equally could go the other way if time allows.
It is possible to take this trip at pretty much any time of year but for the best balance of temperatures, precipitation and visitor numbers, we tend to say that spring through early summer and autumn are ideal. The holiday can be run with almost any number of days and can run in either direction.
The price is per person based on two sharing and includes:
First-class accommodation with breakfast and some dinners
Mid-size vehicle hire
Guided excursions in Porto, Douro, Évora and Lisbon
Portugal Holiday Guide with personal recommendations
Portugal driving guide
Detailed walking notes where appropriate
Pura’s expertise, local contacts, support and advice throughout
International flights are quoted separately for this holiday. Best routings are into Porto (OPO) and out of Lisbon (LIS).
The hotels on this trip are a carefully chosen selection of some of our favourite places to stay in Portugal. You'll stay in an aparthotel in a converted mansion, in an historic Quinta, a pousada (comparable to the Paradores of Spain), and a delightful hotel within Lisbon castle's walls.
For more details, please get in touch to request a detailed PDF itinerary.
It’s important to us that your time in Portugal makes a positive, mutually-beneficial impact on the places through which you pass and the people you meet on the way. By working directly with long-term partners we are in a much stronger position to ensures this happens, maximising the financial gain for them but also enabling us to better introduce you to the ever-changing culture, history and ways of life along the route.
From start to finish, this trip takes you deep into the heart of Portugal's engaging and varied culture. The many layers of Portugal's history are on show wherever you turn, from Roman ruins to the lavish creations stemming from the Age of Discovery and the subsequent wealth it engendered in the country. Architecture, landscapes, food and wine: all tell their own stories and we make sure that you experience a wide variety of each.