12-Day Essence of Portugal Tour: Lisbon, Alentejo, Porto

Lisbon feels as much like a collaboration of villages as a single city. Every neighborhood downtown has something unique and something that excites the imagination. Wander up to Bairro Alto where the streets are packed tight with cafes and taverns. Descend through Baixa and watch the glamour reflecting off the polished plazas. Take a stroll through Alfama, the oldest of the neighborhoods as few other places in the city survived the 1755 earthquake, rising to the panoramic views from Sao Jorge Castle. Along the way, you will discover the poetry of Pessoa, the Carnatic Revolution, and the village-like ambiance that perforates through the city.

After an afternoon at leisure, you savor an iconic piece of Portuguese tradition, a fado performance in one of the old atmospheric taverns. Soulful music escapes through the wooden shutters and into the streets, directing you toward the musicians. The music is mournful, lamenting love, loss, and a life that did not respond to dreams. Two guitars pluck with the melancholy of unrequited lust, and the music takes you on a journey that is only enhanced by the arrival of food and wine. Fado is a national institution, and it originated in Lisbon, with the old village haunts still the best places to enjoy an authentic performance.

Portugal’s architecture holds a past glory. Like the rest of Southern Europe, the idiosyncrasy of design is a major part of its allure. In Belem, you find the greatest examples of Manueline, a local style that took snippets of influence from across 16th-century Europe. Admire the Monument to the Discoveries, then discover the nuance of design at Jeronimos Monastery where parts of the building reflect the styles that were imported. These monuments date to Portugal’s Golden Age while the palaces of Sintra are much older, their Moorish legacy immediately apparent when you see them from afar. An afternoon in Sintra is followed by a relaxed evening that could be enjoyed anywhere in the city. Your guide can make dining reservations as well as drop you off at popular viewpoints and neighborhoods.

Alentejo is Europe as it used to be, where fortress remains dot the hills and medieval towns appear like phantoms on the plains. Rural and rich in history, this is a region that is bafflingly overlooked by the majority of tourists in Portugal. Yet it is the one that is most authentic in its presentation of yesteryear and today. You spend today and tomorrow in Alentejo, starting with a journey through the countryside to Evora. Two outstanding sights set the scene in Evora. Discover the Corinthian columns of the Roman Temple and the endless piles of femurs and skulls in the Chapel of Bones. But keep exploring, and you find that this whitewashed town is worlds away from the 21st century. Everywhere you look there is tradition and there is nothing quite like wiling away the evening on a plaza, feasting on the ham and cheese of the interior.

Traveling with the same guide, you continue the Alentejo adventure, winding across the landscapes that make this region so memorable. Olives and cork have sustained Alentejo for centuries, simple crops that are known across the world - more than half the world’s genuine wine corks still come from here. Spend the morning at a walking farm, sampling the olive oils, and sharing stories. Take a stroll through the cork oak forests, learning how it is harvested and handcrafted into the cork you know. Then enjoy a typically languorous Portuguese lunch at a boutique Alentejo wine estate, the wines paired with the dishes from the region.

There is a fair drive in the afternoon, taking you across the open plains to Obidos, a small, walled town close to the coast. The history stretches back to the Romans, and the initial impression of the castle is quick to suggest grandeur. Enter through the city gate, beneath a beautiful ceramic mosaic, into a city that feels like the 14th century. A maze of cobblestone awaits, leading you through the colors and charms of the past. Everywhere is polished smooth through centuries of footsteps and weathering. And as you slow the pace you find that Obidos is a city that happily remains in the 14th century.

Other walled towns are found close to Obidos, each with a lavish appearance that is in contradiction to their working-class roots. Royal monasteries also hide on the plains, odes to Baroque and Gothic styles. Travel out to the cliffs, and there is a hint of old Moorish culture, along with colorful fishing boats and sublime lunchtime seafood. You spend the whole of today on an adventure around Obidos, stopping at medieval walled towns, cute seaside villages, Atlantic Ocean clifftops, and a monastery that still whispers the story of King Pedro and his star-crossed mistress. Traveling with an expert guide, you find a region that has always remained true to itself, one that happily repels influence from Lisbon or further afield. A dish of fresh barnacles washed down by fruity local wine, is just one of the day’s treats.

Travel north today, meandering across the hills that separate Portugal from the Atlantic Ocean. Stop at the Monastery of Santa Maria, the great Portuguese interpretation of the Gothic style, where flamboyance drips from the archways and mosaic walls. Listen to the legendary tales in Fatima, where a transcendent church spire hangs high above the streets. Stop for lunch at a small seafood restaurant on the cliffs, with time to take a stroll along the windswept coastline. Then keep following the trail north, ascending to Coimbra, a city of incredible Gothic glory. Tomorrow, you will be guided around this old university city. Today, you just need to stroll without a map, the maze-like streets of the old town a place that most visitors could happily spend weeks exploring.

On the outskirts of Coimbra, lies the evidence of older history. Mosaics cover old stone walkways left by the Romans, and their color is faded but not forgotten. Columns stand beside moss-covered walls, and you walk between the houses of 2,000 years ago, discovering a site that was only rediscovered a century ago. Complete the morning in Coimbra’s World Heritage university buildings, finding more architecture to add to the Portuguese puzzle. For many visitors, these seven-century-old university buildings are amongst the finest in the country, a walk through the grandeur of the Golden Age and the Portuguese ability to make an imported style their own.

The afternoon is at your leisure in Coimbra, and your guide is likely to recommend a local restaurant that specializes in the centuries-old pork and potato dishes from the interior, where large platters are served in a tiny little tavern. From this eatery, you complete the cultural immersion with a fado performance, the style in Coimbra very different from what you experienced in Lisbon. Rather than lament lost love, Coimbra’s fado sends out raucous messages of revolution.

The hills become greener and steeper the further you travel north. Stepped vineyards are dotted with farmers, the vertiginous slopes meaning that almost all harvests are conducted by hand. Rivers wind beneath tiny villages, where there are almost as many churches as there are houses. Wine estates await on the highest hills, two of them beckoning you forward for a tasting. This is a World Heritage region that is quick to pull on all the senses, Picnic amid the vines, listen to the silence on the hills, and spend the night in a village that is perched high above the Douro River. Portugal is a country that likes to take things slowly. The north is the slowest part of the country, and your time around the Douro is as leisurely as it comes.

The route to Porto follows the wine terraces, sometimes descending towards the banks of the Douro River before rising high onto the hills. Arrive in the capital of the north, and day ten is all about the old city, a twisting, turning, tempting labyrinth dominated by blue ceramic mosaics. The blissful tiles fill many of the city’s walls, defining the colorful facades and the ambient interiors. Check into your hotel and take a walk in and around the riverfront, stopping to encounter the lush rooms of the Stock Exchange Palace and the gilded brilliance of Sao Francisco Church. The afternoon is at your leisure, and everywhere you turn in Porto offers something for the eyes and the soul.

On day 11, you travel a little further afield. In the morning, the journey is geographical, up into the hills to classy neighborhoods that look down on the river. You will then cross the old bridge to Vila Nova de Gaia, home of the port cellars and a great place to take your taste buds on a tour. Local northern cuisine complements the tasting along the river before an afternoon cruise on the Douro, an idyllic end to this handcrafted essence of Portugal tour. You travel in one of the old wooden boats that used to bring barrels of grapes down from the vineyards, a timeless vessel that is symbolic of the Portugal you have discovered, unique, traditional, and dotted with artistic touches. Your final evening is free, and Porto has some excellent restaurants for a farewell dinner.

Breakfast is at your leisure in the hotel before a relaxed morning for saying farewell to Portugal. Take a final walk around the city, perhaps with time for lunch along the riverfront. Then depart Portugal from Porto’s international airport, taking the essence of the country with you.