Self-Drive Portugal Itinerary: Iconic Cities to Charming Towns

Lisbon loves to provide a welcome, a capital that is full of energy and ebullience. The atmosphere whisks you away, pulling you into a city that can also easily lay on the charm. After a seamless transfer from the airport to your hotel, you have a day at leisure and a chance to wander around the neighborhoods that fill Lisbon with such vitality. Baroque ghouls watch you on open plazas, dishes and glasses pile up on terrace tables, tiny doorways entice you inward, and narrow lanes open onto expressive viewpoints. You can walk between the neighborhoods, and there is a lot to discover when you are on foot. For a more complete introduction, you can ride the number 28 tram, the iconic yellow tramcar that has been rumbling up and down Lisbon for more than a century.

Lisbon is a patchwork of attitude and style, a city that is stitched together by the single tram tracks that ply the hills. Some neighborhoods are tightly packed, like Bairro Alto and Alfama. Others are grand and spacious, the lanes in Baixa and Belem allowing iconic monuments to be visible from afar. Sometimes you ascend, wandering up a steep hill to a castle or terrace overlooking it all. At other times you descend, past the vintage stores and antique boutiques, then onward to the riverfront and a concoction of cafe terraces. On a full day’s tour, you find that Lisbon is more a collection of villages than a collection of neighborhoods, whilst also being a city that equals more than the sum of its parts. You have a private guide today, and how much you see depends on your energy levels. There are various routes that can crisscross the city and even within a few miles, you can explore vastly different villages within the city.

The rental car is dropped off at your hotel and within 30 minutes, the road is devoid of traffic. Take the Vasco de Gama Bridge and head southeast, cruising into the rural pleasures of the Alentejo region. Wheat fields fill the panorama to your left, while orchards and olive groves provide contrasting colors to your right. This is Portugal’s most rural region, where the villages are whitewashed against the plains and the towns have an old-world grandeur to contrast their working class roots. Stop first in Evora, where the Roman Temple provides a photo and the Chapel of Bones creates the first show-stopping moment on this self-drive route. Great piles of human bones fill the chapel, standing in piles that can feel both grotesque and poetic.

Evora is a good place to stop for lunch, a World Heritage City where the cobbles have been polished smooth by centuries of human footsteps. From here, you return to the rural qualities of Alentejo, the town of Estremoz perched on a hilltop above the olive groves. Spend an hour or two in the marble-dominated town, then continue to the frontier where the eighth-century border town of Marvao is perched high on a cliff overlooking Spain. At times, Marvao feels like a ghost town, a pre-medieval legacy on the Iberian Peninsula. At other times, this town feels like another world, a getaway of tiled roofs and bright flowers that compels any visitor to stop and explore on foot.

Portugal’s highest mountains create a national barrier with Spain. They also create a day of adventure as you navigate the winding roads and whitewashed villages. It is a day for landscape photos, almost every turn another viewpoint into the Iberian soul. It is also a day for exploring history’s unusual tales. You can soak up the atmosphere in Castelo de Vide, part Roman spa town and part old Jewish neighborhood of vibrant colors; marvel at the views from Sortelha, a 12th-century village standing above wild landscapes; explore the legend of explorer Pedro Alvares Cabral in Belmonte; then spend the night in the ancient city of Guarda, with a view onto the castle from your centrally located hotel.

Take the road north, winding through the Serra de Estrela, where castles dot the distant hills and walled villages await the curious explorer. Rural Portugal is full of treats, and this self-drive itinerary enables you to veer off the road to destinations that rarely see tourists. In Portugal, they drive on the right, which may be new to some. However, the roads outside the cities are rural and quiet, and you can sometimes go 30 minutes without seeing more than two or three vehicles. Towns are well signposted, and you often see your destination from afar, especially Viseu, today’s first destination on the hilltop.

Standing at an Iberian crossroads, Viseu is a city of sacred art and churches, where the historic center maintains a medieval feel. It is full of tales of occupation and takeover that date back to the Roman era. Vineyards surround the town, and there are some excellent places to have lunch and indulge in a short tasting. Continue across green hills in the afternoon, the pilgrimage town of Lamego a natural stop on the road north to the Casa de Mateus manor house in Vila Real. Then onward to Amarante, where the Romanesque buildings reflect in the Tamega River and the art and architecture is a blend of styles, reflective of the myriad of influence that stretched across Iberia. This is the longest day of driving on the itinerary, and you spend the night in Guimaraes, the first capital of Portugal and a great place to stretch your legs on an evening paseo (walk).

With a self-drive itinerary, you travel at your own pace. Take your time and settle into the rhythm of Portugal by enjoying an espresso and pastry on an al fresco terrace, the local way to start a day. Wander amid the ancient stone of St Michael’s Castle, an epic 12th-century show of power that dominates Guimaraes. Then, spend the day traversing the most traditional of the Portuguese regions, Minho, an area that presents its history with pride. An extraordinary Baroque staircase is one of the attractions in Braga, cascading down the hill and dotted with pilgrims. You could spend a week here and not get around to see all the churches and cathedrals, so pick out a couple like the Archbishops’ Palace before continuing towards the coast and the remarkable panorama of Viana do Castelo. A castle hangs above the waves, and the view from turrets make it feel like you are on the edge of the world. Complete the day in Porto, where you have two nights at a boutique hotel in the heart of the old city.

Leave the car parked underground today and enjoy the sensual delights of Porto. As with all hotels on the itinerary, a secure car park is within easy reach of your hotel room, either at the property or in an underground area nearby. Porto is not a place for cars, some of the maze-like central streets are barely wide enough for the old donkey carts that used to rumble across the cobbles. It is also the home of port, and you can take a boat across the Douro River to Vila Nova de Gaia, where a dozen cellars line up against the water. Musty smells greet you on a cellar tour, so many oak barrels standing in photographic harmony. Various tasting options are available, and it is well worth trying a premium tasting as you get to sample contrasting vintages.

Back on the Porto side of the river, you are enveloped by Baroque architecture and blue ceramic tiles, with intricate scenes painted in mosaic form along the sides of buildings. Palaces and cathedrals reveal the city’s intricate attention to detail, while hidden lanes lead you to Douro wine tasting and Portuguese-style tapas. The cafes and restaurants along the riverfront provide a relaxed space to spend the evening, with some of them specializing in distinctive pork dishes made in the region.

The journey south hugs the coast, rising along cliffs with elegant views across the Atlantic Ocean surf. Stop in Aveiro, and switch to a narrow seaweed-collecting boat, the vessel traditionally used to traverse the canals of this old blue city. Continue to Bucaco Forest, where the arboretum’s trails whisper of monks’ secrets. Follow them on foot, and you come across a palace and hunting lodge, a remarkable building standing in the heart of nature. Into the afternoon, and it is worth taking your time in Conimbriga, a vast Roman town that is still being excavated. The columns and walls are in such pristine condition that it can feel that they were only erected yesterday. You spend the night in Coimbra, a quaint little city that is as artistic as any in the country. If you have time today, then the Coimbra University library is a must, or you can also save exploring this World Heritage Site for tomorrow morning. For an authentic dinner, there is a timeless restaurant that serves old-world fare from the interior in a wonderfully rustic setting.

Fabulous architecture guides you back towards Lisbon. First, the church at Fatima, where crowds of pilgrims gather inside to pay their respects to the Virgin Mary. Then, the monastery at Batalha, a flamboyant display of Gothic design that was the earliest Portuguese site to be added to the World Heritage list. Nearby, Alcobaca has a Gothic monastery of a very different style, far more subtle and serene in its use of embellishment. After the largest monastery in Portugal, you catch another glimpse of the coast, where the cliffs overlook towering waves and the small boats make treacherous journeys out across the surf.

Nazare is the perfect place to stop for a leisurely lunch, especially if you enjoy fresh seafood. With the boats standing colorfully on the sand, you can dine on Portuguese specialties, a plate of barnacles a recommended starter. Continue the journey, and whitewashed city walls lead you toward colorfully painted houses in Obidos, a walled village frozen in a medieval time. Then, it is less than an hour back to Lisbon where you leave the vehicle in the hotel’s parking lot for an agent to pick up. This final evening is another chance to soak up the capital city’s old and new grandeur, either in the crumbling district of Alfama or the broad polished lanes of Baixa and Rossio.

After breakfast, you are transferred to Lisbon International Airport for your homebound flight.