Portugal is made for wanderers. From the top of the Moorish remnants of Castelo de São Jorge, Lisbon cascades downhill in all directions, new paths beckoning at every turn. To the south, the 25 de Abril bridge spans the Tagus River, a ringer for San Francisco’s Golden Gate. Across the harbor, the outstretched arms of the “Cristo Rei” statue remind me of Rio.
I’m at once exhilarated and overwhelmed. Since arriving in the capital, my husband, Tim, and I had hopped trams and traipsed through the Alfama district, where the cobblestoned streets contort into knots. We had taken in the austerity of the Sé cathedral. We had woven around clubgoers in the Bairro Alto.
But even after the perpetual motion of the past few days, restlessness had started to seep in. Something about the city stirs up my need to move. It’s not just me: Legend goes that Lisbon got its start when Odysseus, the mythical Greek warrior, passed through, and vagabonds have gravitated here ever since.
In the 15th and 16th centuries, Portuguese sailors expanded the mapped world by setting off from Iberian shores: Vasco da Gama headed south, arriving in India after navigating around the Cape of Good Hope, while Ferdinand Magellan pushed west, his expedition completing the world’s first circumnavigation.
As a child, dragging my finger over the globe, I retraced those intrepid men’s routes. As an adult, I’m always dragging friends down alleys in search of the authentic. So when I learned that Portugal’s coastline south of Lisbon was among its least visited regions, Tim saw the telltale glint in my eyes. He was sold when I told him that our end point, Sagres, sits on a precipice jutting into the ocean near Europe’s southwesternmost point. Early navigators once considered it the “end of the world”—a romantic grace note to this trip marking a dozen years together.
Before we embark on our voyage, though, we need to get out of the parking lot at the Lisbon airport. Tim hasn’t driven a car with a manual transmission in over a decade. So here we are, bucking in our seats as the car stalls. If only we had a fleet of ships instead of this Fiat. Though I’m hoping Nüvi, our smooth-talking GPS, will do us more good than an astrolabe and sextant.
“You know what you’re doing, right?” I ask, and Tim shoots me a sideways glance while tapping the gas. All of our plans hang in the balance—really, in the clutch. Something tells me the mapping of the New World would have turned out different if there had been more marital bickering involved. “I’ve got this,” he says, and the car roars to life, and we lurch forward.
Soon enough we’ve made it to Belém, a historic district on the outskirts of Lisbon that served as the launching point for hundreds of voyages. Engravings of sea mermaids writhe on the facade of the Jerónimos Monastery, a World Heritage site where da Gama’s body now rests.
The mural in the adjacent maritime museum shows Prince Henry the Navigator (1394-1460) surrounded by knights and geographers as he unscrolls a map. Though many historians contend that his reputation was exaggerated, the prince financed numerous fleets and played host to prominent astronomers, cartographers, and scientists at his legendary nautical school in Sagres. “These guys are no match for Nüvi,” Tim jokes.
We grab some fuel—a pair of cinnamon-sugar-dusted custard tarts at the nearby Pastéis de Belém—for the climb up the Padrão dos Descobrimentos. A monument to Portugal’s role in the age of exploration, the huge edifice points out toward the water like the bow of a ship.
To our west the iconic Tower of Belém stands guard over the harbor as it has for nearly 500 years. The limestone fortress incorporates design details from Morocco, Venice, and India, inspired by da Gama’s journeys. A carving of a rhinoceros commemorates the real one that India gave Portugal as a diplomatic gift in 1515.
All of which reminds me: We need to keep moving. After another round of wrangling the clutch, our silver car kicks into gear and we slide over the wide red bridge south under the Cristo Rei’s open arms.
Thirty miles away is the port town of Setúbal, known for dolphin sightings and fresh seafood. It’s getting late in the day, and Tim is starving. “Just a bit farther,” I insist. I’m determined to get dinner in Portinho da Arrábida, a tiny village I’ve spotted on the map amid the cliffs and coves of Arrábida Natural Park.
As the Fiat hugs the limestone rock face and we gain elevation, a forest of cypress and magnolia trees unfurls below. The village is nearly empty when we pull up, save for a few stray dogs and a handful of backpackers. A yellow dinghy bobs in the water. The horizon turns indigo, and I grimace, worried I’m setting us up for a dinner of emergency granola bars.
But we’ve arrived just in time. At one of the seaside cafés, our waiter jabs a finger toward the menu listing for fish stew—the only thing still available. Seated on the patio, we have the view of the water to ourselves. A few minutes later, a steaming bowl of shrimp, mussels, razor clams, and rice arrives, and we dig in, sucking the heads of the shrimp.
The next morning, the two of us drive aboard an acid green ferry to the Tróia Peninsula, a tourist enclave of golf courses, modern hotels, and white-sand beaches. We claim a stretch of sand in Comporta, then sip cocktails in the Ilha do Arroz café, a setting so stylized it could have its own Instagram filter. It’s tempting to give in to this shade of paradise, but perfection isn’t what I’m after. As I scan the water for bottlenose dolphins, Tim picks up on my signals and can tell I’m ready to move on.
So we return to the road and push farther south, where the marshy rice paddies give way to the rolling hills of Sines, the birthplace of da Gama and now home to a modern arts center. It’s the last dose of contemporary life we’ll have for a while; here begins the truly wild coastline of the Alentejo.
Tim pulls over for a break, and I spot the signs that mark the Rota Vicentina, a recently built network of trails delineating some 200 miles of the southwest coast. Our choice is between the blue and green Fishermen’s Trail, which winds along the cliffs, and the red and white Historical Way, which re-creates paths medieval pilgrims took through cork forests and fields of heather.
We hike for an hour overlooking the Atlantic, then linger to dangle our feet off a cliff’s edge. For the first time all week, my brain stops plotting our next move. Minutes float by as we get lost watching waves struggle to splash us from below.
As we drive south, cows graze along the highway. In Vila Nova de Milfontes, a small fishing village that endured repeated attacks by 16th-century pirates, we park and walk down to the water, following the aroma of Restaurante A Choupana, which we find tucked behind a police station.
On stilts along the ocean, the thatched-roof restaurant is surrounded by orange cacti flowers that glow like the embers of the grill the spot is known for. Inside, children with ice cream cones dash between picnic tables. The chef flips chicken and sardines over the coals.
Virgilio is our waiter. “Like the poet,” he says, bringing us a silver plate of steamed clams and the seared catch of the day. He grabs our camera off the table and makes us pose. “I take great pictures,” he says, framing a series with the surf crashing behind us. Even cheesy snapshots have the flair of poetry in this setting.
That evening, we check in at the Herdade da Matinha, a country house two miles down a dirt path off the highway. I had found the place with the help of Casas Brancas (named for Portugal’s whitewashed inns), an association of independent lodgings, restaurants, and outfitters in the Alentejo.
The nonprofit’s Marta Cabral told me that this region was long overlooked as a poor and sparsely populated swath south of Lisbon. But the Alentejo has emerged as an authentic alternative to the crowded beaches in the Algarve region farther south, she explained—a bastion of rural hospitality.
Owners Monica Belezza and her artist husband, Alfredo Moreira da Silva, cook all of the meals at the inn; da Silva’s colorful canvases accent each room. Tim and I pick oranges from the trees and eat them alongside the lap pool. After a dinner of roast chicken, grilled eggplant and sardines, and Portuguese wine, we spend the evening curled up by an outdoor fireplace. “I’m not sure I want to leave,” I say.
The next morning, we find da Silva in swim trunks standing on a ladder in the dining room, hanging a surfboard over a doorway. Belezza is standing by, carefully monitoring his balance. “We lived in the center of Lisbon, and always thought it would be nice to have a restaurant in the country,” she tells us. “We thought, ‘Let’s move to Australia’—then visited this part of Portugal and realized we could have that rugged diversity here.”
Their bliss is contagious. “Do you think we could open an inn some day?” I ask Tim. He smiles. “Do you think you could handle slowing down?” He makes a good point. Yet I feel an unexpected urge to put down roots and let travelers come to me.
But for now, we return to the mission at hand: the final stretch toward Sagres. We navigate mountain switchbacks, past the cliffs of Zambujeira do Mar and through tunnels of pine and eucalyptus trees. These give way to valleys scattered with cattle, then hillsides dotted with wind turbines.
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We’ve reached that part of a journey where conversation would only get in our way. VW vans coated in dust carry surfboards on their roofs. As we coast into the Algarve and past the town of Vila do Bispo, I see what looks like quicksilver on the horizon. It’s the ocean. Then I do a double take: Is that an armada of windsurfer sails bobbing just a few hundred yards away? No, they’re on land, harnessing the wind on wheels, not waves.
Finally, we reach the windswept edge of Europe at Sagres and wander among fortress relics. A placard identifies Atlantic, Mediterranean, and African bird species, a mix not found elsewhere in Europe.
Tim notes the merging of worlds: Romans named this place Sacrum (“holy”), later drawing Christian pilgrims. Some are said to have stuck around to attend Prince Henry’s navigational school here. All that remains is a church, a few brittle buildings, and a massive circle of stones. As for its function, the best guess is a mariner’s compass.
A white stork glides above our heads, and we try to avoid vertigo looking down the 250-foot cliffs, only to notice a man fishing off the “end of the world.” There’s a tug on his line, and he grabs his rod between his knees—it’s a big one. The man strings a basket on the line and sends it down. Standing on the edge with the grace of a tightrope walker, he gently pulls on the line, maneuvering his catch into the basket. A few seconds later, the basket reappears, a silvery sea bream squirming inside. He pulls it onto the rocks. We clap; he raises his fists in victory.
“How long have you been here?” a man asks him.
“Two hours, and two fish,” he says. “And they’re big fish.” He smiles, wraps them in a bag, and packs up for the day.
We take his cue. Tomorrow will bring more fish—and more discoveries. Today belongs to this cliff, and to each other.
Janelle Nanos, a former editor at National Geographic Traveler, penned this feature, which first appeared in the magazine’s August/September 2014 issue. Follow Janelle on Twitter @JanelleNanos.