Portugal’s Alentejo: Hilltop Palaces, Castles, and Cathedrals

The castle keep of Monsaraz. Francisco Antunes/CC-BY-2.0

There was a time when this was the ragged edge. The front lines. When invaders could come from the south or the east, by land or sea. When the responsibility for defending king and country—and all that was sacred—rested with a series of hills and the battlements built on their crowns.

Standing atop the castle walls in Monsaraz, I could see for miles. Patchwork fields, tiny towns, and one of the largest artificial lakes in Europe were all at my feet. And just over there, an invisible line divided two nations, with Spain almost literally a stone’s throw away. Once, the territory below me was indeed a very dangerous place—no-man’s land, a spot scrutinized by the soldiers stationed here, searching for threats from abroad. Today, it’s totally peaceful and one of the most beautiful places to visit on the Iberian Peninsula.

Many visitors begin their visit to Portugal in Lisbon, the country’s capital and largest city. And from there, the vast majority head either north or south. To the terraced landscapes and crisp wines of Porto and the Douro Valley. Or to the long stretches of beaches, cliffs, grottos, and caves lining the Atlantic coast in the Algarve. And you can’t blame them—those regions are lovely and offer plenty of pleasant pursuits.

Exploring Evora

Bruno Garcia/Unsplash

The striking conical spire atop the Cathedral of Evora. Jiri Macek/Unsplash

But on this summer road trip, I was headed southeast, toward the Spanish border. Delving into the heart of Alentejo, Portugal’s largest region, I was in search of hilltop palaces, castles, and cathedrals. I based myself in the capital, Evora, home to a little more than 50,000 people. After arriving and settling into my small hotel (a pleasant, stylish place with tidy rooms and a rooftop pool), I ascended the cobblestones to have a look around.

First, the bones. Celts, Romans, and Moors all left their mark on Evora, a hilltop city that has been inhabited since the second century B.C. The old city is encircled by walls that were first built in the third century A.D., although pretty much everything you can see today dates to the Middle Ages. As a construction project ordered by King Afonso IV in the 15th century, these walls once delineated the limits of the medieval city.

I walked through a gate still brimming with battlements. Inside, many treasures are preserved as part of a UNESCO World Heritage Site. Right at the top of the hill, the columns of the Roman Temple of Evora, also referred to as the Temple of Diana, still stand. That name is actually more of a nickname—historians and archaeologists aren’t sure, but most think this temple was actually dedicated in the first century A.D. to worship the Roman emperor. Either way, with its line of columns and Corinthian capitals, it looks a little out of place in Portugal, such as a well-preserved ruin you would find in Rome or Athens.

The Roman Temple of Evora. Jose Santos/Unsplash

Much later in Evora’s evolution, a golden age began. In the 15th century, the Portuguese royal family made this city their residence on a semi-permanent basis. The rest of the country’s aristocrats and elites followed suit, and a building boom took place. Evora’s old city is still filled with palaces, churches, and a handsome cathedral.

And yes, the bones. Arriving at the chapel, little signs translate exhortations penned by poets of the past, encouragements to pause and reflect on the transience of life. Lovely reflections, sure. But I still found the Chapel of the Bones a little chilling. Built in the 16th century from some 5,000 bodies, an inscription (in Latin) over the door welcomes visitors: “We bones are here waiting for yours.”

Although sinister in appearance, the Chapel of the Bones was meant for reflection on the transient nature of earthly life. Miguel Alcantara/Unsplash

Part of the Royal Church of St. Francis, they were disinterred from local graveyards when other buildings needed the space. For the Franciscans who built this place, it also served as a handy way to remind the affluent townspeople that they should focus their attention on their souls and their final destination rather than material things. Today, whole walls remain that are built with skulls, and columns with bones from arms and legs. It’s dark, creepy, and wonderful.

Castle on a Hill

On a clear day, from atop Monsaraz Castle, one can see even as far as Spain. Lea Poisson/Unsplash

I could have spent a week just enjoying Evora. But soon, it was time to get out of town. Driving through reddish rolling hills lined with vineyards, I was looking for castles. On a previous visit, I had spent time in nearby Estremoz. Then, winding to the top of the hill, I navigated up a thin, sinuous one-lane road and squeezed through a narrow entrance in the castle walls, parking near the pillory. Here, you can stay at an actual castle—which I did.

Now turned into a “pousada,” it’s a place preserved by the national government and offering accommodation. The castle was originally built in the 13th century for Queen Santa Isabel. The halls are still lined with old statues and rich, if slightly puzzling, oil paintings. After dark, an almost ghostly feeling descends on the place—all those centuries of history, just hanging in the hallways.

I slept well in what once may have been a room once occupied by a royal. And the next morning, a climb to the top of the castle tower took me to vertiginous views of the almost-perfect town below. Spires and steeples and terracotta roofs. Chapels and monasteries.

But today, I was headed for Monsaraz—the area’s ultimate castle town. Its hilltop location has been coveted since Neolithic times, and settlement there dates back to prehistoric days. Looking down on Spain right on the fronteira and not so far from North Africa, the village was the site of fierce fighting with the Moors, who first took the site in the eighth century A.D. The town went back and forth in battles in the 1100s and 1200s and was finally won by Sancho II, king of Castile, León, and Galicia with the help of the Knights Templar. In a rather grand gesture of gratitude, he gave them the town.

Today, it’s just a spectacular place for a stroll. The main street straddles the summit of the hill and is lined with small shops, wine bars, and flower boxes. Foot traffic was thin, and the whole light-infused place was placid and quiet. The Watchtower of São Gens do Xarez rises at the end of the road. Every one of the little cross streets falls away into thin air, the surrounding countryside far below. It’s like a castle town in the clouds.

I had a lot more to do that day. But first, a beer at an open-air bar with a view. A place fiercely fought over for many centuries is now providing, for me, a beautiful moment of peace.

When You Go

Fly: Lisbon’s Humberto Delgado Airport (LIS) is the main hub for TAP, Portugal’s national airline, which flies nonstop to a number of North American cities, including Chicago, Boston, Montreal, Toronto, and New York.

Getting Around: While Evora itself is compact and all of the sites can be easily reached on foot from any reasonably central hotel, you'll definitely need a car to reach other castle towns, including Estremoz and Monsaraz. Plan well ahead if you can only drive an automatic transmission—the vast majority of rentals in Portugal are manual. Europcar is one agency with a location in Evora.

Stay: Vitoria Stone Hotel is a lovely, small hotel just a few steps from Evora’s medieval walls. Rooms are cozy but super-comfortable. Service is personal—the front desk staff will often remember your name and greet you in a friendly fashion when you return from a long day of touring. And the rooftop pool (with bar service) is the perfect place to recharge.

Take Note: If you don’t want to drive on the busy streets of Lisbon, Evora is easily reached by rail—it’s a painless 90-minute ride. Enjoy the views out the window of the rolling countryside, and once you arrive in town, you can rent a car. Book your train tickets online at CP.pt/passageiros/en/buy-tickets