This Portugal Mountain Range Is Home to Tiny Medieval Towns, Locally Made Beer, and Hidden Swimming Holes

Courtesy of Center of Portugal Tourism Board Dining amid the barrocais, or “chaos of blocks,” in Monsanto.

After driving up to the summit of Torre, the highest peak in Portugal's Serra da Estrela mountain range, I had a childlike urge to climb even closer to the clouds. I spotted a narrow concrete plinth and hoisted myself onto it. Finding my balance, I raised my arms shakily in triumph. "Do you realize," I called down to my girlfriend, Diana, "that I'm higher up than every single person in continental Portugal?"

She rolled her eyes, unmoved. Never mind that we'd driven up a long, winding road to Torre's summit. Diana had been skeptical of my idea to head straight for the mountains. This was, after all, a country shaped by the Atlantic Ocean, with coastal cities, balmy beaches, and seafood in abundance. Now, I felt vindicated.

All that climbing and driving had left us famished, so we scoured the Centro Comercial da Torre (351-911-546-037), a cramped general store filled with cured meats, sheepskin-lined clothes, liqueurs, and local dairy products. I bought a loaf of bread, a chunk of tangy cheese, and two seven-ounce bottles of Super Bock, the unofficial beer of Portugal.

Outside the store, sitting on its sweeping back deck, we could hear the skeletal chairlift of the country's lone ski resort, idly twisting in the wind until next winter. The aging towers of the abandoned observatory glinted in the summer sun. We ate our peaceful picnic while staring out at the drama of the Serra da Estrela.

That morning, we'd driven nearly three hours south from Porto through the Centro region, which stretches across the heart of Portugal from the Atlantic Ocean to Spain. We wanted to explore the rugged environs of the Serra da Estrela, and get a sense of the area's rich history.

In the 1600s and 1700s, the Portuguese-Spanish border was a violently contested battleground. Settlements were transformed into fortified villages, strategically located on hilltops; some date as far back as the 12th century. Today, 12 of these towns make up a government-designated network known as the Historical Villages of Portugal.

Luis Pina Photography/iStockphoto/Getty Images The Cov?o dos Conchos, west of Belmonte in the Serra da Estrela, diverts water to the larger Lagoa Comprida through a large spillway and tunnel.

We hadn't factored white-knuckle driving into the equation. With me behind the wheel and Diana in the passenger seat, we drove 45 minutes down the zigzagging road from Torre, stopping at a 25-foot bas-relief sculpture carved into the side of a mountain. The work depicts Senhora da Boa Estrela, the protector saint of the shepherds. We parked on the roadside and ascended a small set of stairs to the statue's base, looking up at the two-story saint in awe.

Our final destination that day was Belmonte, a city of 7,000 built around a Roman-era castle. We checked in to the Pousada Convento de Belmonte, a 13th-century monastery that has been converted into an elegant hotel. The building's ecclesiastical past gave it an air of weighty stillness. The living room had once been a chapel, and still had a vaulted ceiling. Diana and I spoke in hushed tones, as if back in Sunday school, and slept deeply in our tranquil bedroom. In the morning, we watched from the stone-lined swimming pool as the sun rose over the jagged peaks of the Serra da Estrela.

Refreshed, we got back in the car and drove toward the castle, past houses decorated with flowering window boxes. Little more than the exterior walls of Belmonte's castle remain. From its ornately carved window, looking out over the green shades of the Zêzere valley, I tried to picture the medieval past, the armored knights who once protected the structure. We drove to the Torre de Centum Cellas, a crumbling structure from the Roman period. Historians have never been able to determine whether it was used as a temple, a prison, a villa, or something else entirely. Its open-air ruins reminded me of a crown, the battlements silhouetted against the purple sky.

In the early evening, we set out for the Quinta da Barroquinha, a quaint cottage set on a seven-acre farm near Vale de Prazeres and the perfect home base for the next two nights. The cottage had once been a shepherd's hut; the rough stone walls and woodstove showed its past lives. After our host welcomed us with a small bottle of olive oil made on the property, Diana and I cooked pasta and split a bottle of Portuguese red on the patio. As we ate, the scattered lights of the valley gave way to twinkling stars.

After stopping for breakfast the next morning in the nearby town of Alpedrinha — by now, "pastéis de nata" and "café, por favor" had become our daily refrain — we drove up a rocky hill to Monsanto, a village that is built beneath, between, and atop enormous granite boulders. The tiny cobblestoned lanes are too narrow for cars, so we walked through the streets marveling at the stone walls. We saw a house with a roof formed by a globular mass of granite. Boulders on either side of another property squeezed it like a corset. One home was carved directly into the rock, with a low-slung wooden door.

From the impressively preserved ramparts of the castle that crowns Monsanto, we could see for a hundred miles in any direction. Birds floated on the wind at our eye level; the sun was strong overhead, and we felt beads of sweat on our foreheads. To get out of the heat, we skittered downhill to the homey Taverna Lusitana. We sat on its terrace at a minuscule table, on seats that had been carved out of boulders, and shared a pizza and beers from the taverna's own brand, Cerveja de Guerreiros. The ice-cold mugs soothed our sunburned faces. In the corner of the terrace, an artist was sketching the valley. The drawing depicted everything from the stretch of land below to the village's barrocais, or "chaos of blocks," that shape several old towns like this across the region.

After leaving Monsanto, we explored Castelo Branco, a Templar stronghold that dates back to the early 1200s. All that remains of its castle is a wall and two crumbling towers. The garden, Jardim do Paco Episcopa, verdant and blooming, brought the whole experience to life for us. We wandered through the maze of waist-high hedges to a chorus of delicately trickling fountains, imagining the lives of the first inhabitants.

Courtesy of Center of Portugal Tourism Board The town of Castelo Branco, Portugal, dates back to the 13th century.

A short drive away, we arrived at a remote village, Penha Garcia, where a well-worn path brought us to the highest point in town. From there, signs directed us on a two-mile tour through a series of narrow streets.

We passed old mills, rocks containing fossils that locals called "painted snakes," and a natural pool. We hadn't thought to bring bathing suits and towels, so the water's alluring, blue-green tint may as well have been a mirage. But looking at the map, we saw that farther down the gorge lay another, more isolated body of water, a man-made reservoir ringed by an empty beach.

A bumpy off-road drive tested our rental car's mettle, but it led us to this quieter spot. Alone but for the pine trees rustling in the summer breeze, we decided to skinny-dip in the placid pool. As I swam in lazy circles, Diana retreated to the shore to eat cheese and smoked sausage. When I looked back at her, she was holding a lemon she'd plucked from a tree, as round and large as an apple. The past was tangible here, on a remote edge of Portugal, in the shadow of an ancient castle.

A version of this story first appeared in the July 2022 issue of Travel + Leisure under the headline "Time Travel."