There are heaven-sent times to ride a bicycle in Portugal's Alentejo region, a Belgium-size swath of land southeast of Lisbon where cork orchards, whitewashed towns, rustic food, and ancient stones are plentiful. Spring, for instance, when carpets of wildflowers erupt and white storks return from Africa. Or autumn, when the first evening fires are lit and black Iberian pigs are loosed upon the acorns.
But in early September, during one of the hottest spells anyone could remember, I was pedaling through a living furnace. The day had started promisingly enough, beneath stately castle walls in the medieval town of Montemor-o-Novo. But after 45 miles, the temperature had climbed above 100 degrees. Separated from my group — too fast for some, too slow for others — I rolled along the blistering tarmac, straining up each hill. When I asked Junior, my jovial and faithful young guide, how much farther we had to go, he seemed to fumble for an answer that was credible yet wouldn't crush my spirit.
At one point, I thought I could see our destination, the Torre de Palma Wine Hotel, across the shimmering plains. But in a trick of perspective like some diabolical Magritte painting, the road never drew me closer. I detected the faint tremors and cruel chills of heatstroke. I drank water and poured more over my head. Junior suggested sniffing it up my nose, as if to cool my burning face from within.
I'm a keen cyclist, and have suffered through gorgeous scenery on a bike plenty of times. But this was a new level of hurt. To distract me, Junior kept talking: "So, where are you from?" I was too miserable and out of breath to answer. Every few miles, I pulled over to one of the gnarled, solitary trees beside the road, flopped in the anemic shade, and tried to quell the buzzing in my head. Finally, I made a command decision: "Call the car."
There's no shame in summoning the "sag wagon," as riders call it, but at that moment it was miles back, servicing others. I was in the horns of a dilemma: complete the last six miles to the hotel or wait in the heat. Were there no gas stations where I could find the salve of a Coke or a frozen treat? "That's the thing about the Alentejo," Junior said stoically. "You can ride for twenty or thirty minutes in any direction and see nothing."
I got back on the bike. Most of the rest of the way seemed to be uphill. Junior, steady as a stone, rode alongside, pushing me with his free hand. I pictured the cover of my college copy of Don Quixote: the delirious knight and his stalwart sidekick riding through an arid landscape. Cresting the last hill, I coasted to the hotel, where someone pressed cold towels into my hands. I looked sheepishly at Junior and finally answered his question: "New York."
Riding the Alentejo had been a fantasy of mine since a visit with the Swiss architect Valerio Olgiati at his neo-Brutalist villa among the cork oaks of the western part of the region. Marveling at the expanses surrounding us, Olgiati enthused that one could drive all the way to Madrid on dirt roads. It was true, he allowed, that the Alentejo, like Portugal itself, was becoming more fashionable, attracting the likes of Philippe Starck and Christian Louboutin, both of whom own homes near his. But the land still feels unusually wild for Europe.
Fortunately, this magnificent countryside also has plenty of quiet, well-maintained paved roads, which are ideal for riding. As I listened to Olgiati, I thought of João Correia, a Portuguese native and former professional bicycle racer based in Marin County, California, where he runs the high-end bike-touring company InGamba. Its conceit is simple: guests get to play pro cyclist during the day before retreating to a vineyard or other bucolic setting for a chef's-table dinner. As cycling gets older and wealthier (certain riders like to call it the new golf), such excursions, combining endurance and epicureanism, have grown increasingly popular.
I called Correia, who'd recently begun running trips to the Alentejo, to inquire about going in September. "You know it will be very hot in the interior at that time?" he asked. (InGamba normally takes groups to the area in April and October.) But September was what worked for me and, more importantly, my family. My wife and seven-year-old daughter's patience for my extended bike journeys had worn thin, and so, as a gesture of appeasement, I wanted to bring them along — not to ride, but simply to enjoy the region.
Correia arranged a small group trip that would cover a little more than 300 miles in a week, from the tip of the Tróia Peninsula, just south of Lisbon, through cork farms, vineyards, and Roman ruins, to the village of Évora, a UNESCO World Heritage site. And so, a few months later, we found ourselves on a high terrace of the 17th-century Palácio Belmonte, the beguiling hotel where Wim Wenders filmed scenes for his 1994 film Lisbon Story. Spreading out below us was the historic Alfama district, its warren of streets punctuated by the graceful dome of the Panteão Nacional. In the distance, we could see the big blue band of the Tagus River. In Portuguese, Alentejo means "beyond the Tagus," so it seemed appropriate for us to begin here, on the other side.
And it was particularly important to Correia that we begin at the Belmonte. "You're in a hotel, but not really," he told me. I could see what he meant. As I wandered the ornate, high-ceilinged rooms with my daughter in search of a chessboard and a bottle of port I'd seen earlier, I felt as if we were visiting the estate of an eccentric relative. In the narrow cobblestoned streets outside, an incessant stream of visitors to the São Jorge castle passed on foot or in noisome tuk-tuks belching exhaust. But behind the huge red doors of the Belmonte, we could shut out the city and, it seemed, the past few centuries.
The next morning, our cycling party gathered in the lobby. My fellow riders were three couples, all American. Rather than navigate Lisbon's hills, traffic, and tram tracks, we climbed onto a bus for the seaside town of Setúbal. There, after a lunch of sea bass and sardines at Tasca da Fatinha, a waterfront tavern, we boarded a ferry to the Tróia Peninsula, where the InGamba crew and a neat row of very expensive Pinarello Dogma F8 racing bikes were waiting for us.
It was a brilliant blue afternoon, with cool ocean breezes from the west. Every cycling expedition begins with a "shakeout" day to see what's working and what's not — with the riders as much as the rides. Our pace was casual and chatty. We discussed a procession of gaily painted boats adorned with religious statuary. When a scooter whined past, one of the guides, a recently retired pro named Manuel Cardoso, jumped into its slipstream — "motor pacing," as racers call it. We finished with a climb to our hotel, the Pousada Castelo Alcácer do Sal, located in a former convent in Alcácer do Sal, a town that was central to the salt trade during the Roman Empire.
On the second day, we turned inland, away from the marshes and pine forests of the coast. Cork oaks dotted the hillsides, floating like delicate green clouds above the brown grasslands. As I settled into the rhythm of the ride, I found that the greatest pleasure, even more than the scenery and the camaraderie, was being freed, thanks to the support team, from all worry. In the morning I simply had to report for my daily briefing with Cardoso. There sat my bike, tuned and polished, with fresh water bottles and a Garmin computer loaded with the day's route map. Nearby was a spread of rice cakes, energy bars, and the delicious Portuguese custard tarts known as pastéis de nata. If I flatted or got thirsty on the road, the support vehicle would whisk up with a fresh wheel or bottle. At the end of the day, I handed my bike to the mechanics, put my sweaty clothes in a mesh bag on the door handle of my hotel room, and reported to the soigneurs for a massage.
Soigneur, a French word meaning roughly "one who provides care," has special resonance in the cycling world. "The mechanic takes care of the bicycle," as Correia explained, "and the soigneur takes care of the rider." One of ours, José, had the thoughtful mien and close-cropped beard of a noble from a 17th-century Portuguese portrait. He worked my savaged legs with the intensity of a monk.
The true heat began on the third day. The chatter subsided, the pace slowed, and we were all content to let the pros up front take the brunt of the wind. Had I not been so focused on reaching the Torre de Palma without passing out, I might have wondered how my wife and daughter were getting on. I needn't have worried. When I finally did arrive, I found them emerging from a swim, having already taken a cooking class with the hotel chef.
Torre de Palma, which opened in 2014 on a 13th-century herdade, or estate, consists of stark white buildings, old and new, surrounded by agricultural plains. At sunset, we joined the owner, Paulo Barradas Rebelo, for vinho verde atop the property's eponymous tower. It had a vaguely Moorish cupola and notched openings around the top, through which I imagined medieval archers flexing their bows. "The families liked to show their power with symbolic gestures," Rebelo said. "From here they could keep an eye on the workers."
After Rebelo pointed out the Roman ruins in the distance, my daughter begged to go for a visit. We borrowed cruiser bikes from the hotel and pedaled along a gravel road to the gates, only to find them locked. Then we spotted a small opening, and in a moment of parental-role-model failure — I blame the heat — I decided we should sneak in for a quick look at the ancient frescoes and olive-oil presses.
Our group left earlier the next morning, to avoid the worst of the sun. Scenes unfolded before us like a mildly narcotic dream: the symmetrical play of vineyards across reddish hills, a man on a horse-drawn cart laden with grapes. We breezed past the ornate gates to distant estates and countless whitewashed houses accented with ultramarine or ocher. We stole into centuries-old villages where old men with walking sticks eyed us. Occasionally, a car passed by, the driver shouting words of encouragement (or so we hoped).
At the end of the fourth day, we rolled into São Lourenço do Barrocal, a vast estate reached by a dirt road lined with holm oaks and carob trees. For generations it was a farm belonging to the family of José António Uva, who left a job at Saatchi & Saatchi to turn it into a hotel. Like many other properties in the region, including Torre de Palma, it was expropriated by the communist government in 1975 after Portugal's Carnation Revolution. It took until 1991 for the family to regain complete control of the land.
In 2002, Uva embarked upon what would become a 14-year restoration project of São Lourenço do Barrocal. By then the long, white buildings had broken roofs, and their only inhabitants were pigeons. Uva was obsessive about realizing his vision for the hotel. Wanting, for example, to reclad the roofs with original rust-red Alentejo tiles, which are no longer made, he recruited a truck driver to find caches on his routes, collecting some 300,000 over two years. He also enlisted high-end partners of the sort one might expect of a former advertising executive, including Pritzker Prize–winning architect Eduardo Souto de Moura and Monocle publisher Tyler Brûlé's Winkreative agency, which oversaw the branding. The reborn São Lourenço do Barrocal is an appealing mix of comfortable rusticity and contemporary minimalism. Our post-ride massages at the hotel's Susanne Kaufmann Spa took place within small chambers painted entirely white. The ceiling hooks overhead were the only reminder that the spaces had once been used to dry hams.
With Barrocal as our base, our group spent the next few days riding through the surrounding countryside. We climbed to Monsaraz, a stunning hilltop village with narrow passages, a castle with an old bullring, and views of Spain —everything, seemingly, but hordes of tourists. There, I met Thierry Bernard, a French expat who had stocked his shop, Casa Tial, with delicacies like liqueur made from poejo, or pennyroyal, a popular local herb.
I asked what had prompted him to leave a fashion career in Paris to come to this town of 780 people. "The Alentejo calls you," he said. "There is something here that people really connect with." I felt that something on a sunset walk at Barrocal when we happened upon one of the Neolithic menhirs that dot the property. Still warm with the day's heat, the huge curved stone jutted up from the grass. Beyond this dormant sentinel, the fairy-tale visage of Monsaraz shimmered in the distance.
With the heat wave subsiding and our bodies acclimating to the rigors of daily riding, a sense of joviality returned to our group. We would start out easy, with sing-alongs of 1980s hits. But for some — and I am implicated here — a bike ride is a race spoiled, and so, after a break for coffee and snacks, someone would inevitably make a move, inviting the others to chase. Later, after returning to Barrocal, we would happily devour plates of watermelon, thick bread with tangy Serpa cheese, and salads topped with huge wedges of tuna.
My wife and daughter, meanwhile, had been doing some riding of their own with Filipe Gomes, Barrocal's courtly, elegantly dressed horseman. "The Alentejo is my heart," he said. "The horses, they are like my sons." In the afternoons, I'd meet up with my family to go exploring. In São Pedro do Corval, we found Rui Patalim, a fifth-generation potter, in his workshop. My daughter watched, transfixed, as he whipped off a mug, barely seeming to move his hands. In the nearby village of Reguengos de Monsaraz, we wandered into Fábrica Alentejana de Lanifícios, the last producer of traditional blankets in the region. Inside a century-old blue-and-white building, originally an olive-oil factory, a woman worked looms as old as the beams above her.
On the final day of the ride, the group pedaled into the town of Évora, whisking past the Roman Temple of Diana at the center of town. That evening, I returned — by car, thankfully — to Monsaraz with my wife and daughter. At an outdoor table at the Sabores do Monsaraz restaurant, with a spectacular view of the enchantingly lit city, we ate platters of black Iberian pork and bacalhau, followed, at the urging of the matronly owner, by glasses of white port and cake. Festive horn music played as people wandered the old walled town, their shadows dancing on the walls.
Back home in New York, I found myself missing the camaraderie of the ride. There is something especially rewarding about undertaking a physical challenge, in an intriguing new landscape, with a group. Evidently, I wasn't alone in feeling that way. For weeks, we all kept bantering on the team WhatsApp account. "Guys," Correia chimed in, "you know the ride is over, right?" Real life was calling — work, the start of the school year — but we couldn't keep from dreaming of the next Alentejo hill to climb.
The Details: What to Do in the Alentejo
From Lisbon, the town of Alcácer do Sal, on the edge of the Alentejo, is about an hour’s drive southeast. Évora, the region’s principal city, is about an hour and a half east.
InGamba: Each of this bike-tour specialist’s all-inclusive trips is accompanied by a team of mechanics and soigneurs, as well as support vehicles. The first-rate dining and accommodations are the perfect reward after a day on the road. seven days from $7,450 per person.
Palácio Belmonte: Staying in one of the 10 suites at this historic boutique hotel will leave you feeling aristocratic. Once a family villa, the property, which overlooks the Tagus River, has interiors rich in antique details, including thousands of stunning Portuguese tiles. Lisbon; suites from $560.
Pousada Castelo Alcácer do Sal: Set on a hill in Alcácer do Sal, this property occupies a 16th-century former convent. Be sure to dine in the restaurant, which serves standout regional dishes like pig-ear salad. doubles from $145.
São Lourenço do Barrocal: A recently opened property at the heart of a historic, 2,000-acre estate. The rooms open onto rolling hills dotted with cattle, ancient megaliths, and crops ranging from olives to grapes used to make São Lourenço’s own wines. Guests can ride cruiser bikes, sample cheeses, or stargaze at a nearby observatory. Monsaraz; doubles from $220.
Torre de Palma Wine Hotel: This renovated 13th-century plantation sits in the eastern Alentejo town of Monforte. Ride Lusitano horses past the ruins of a Roman villa or recline poolside as you gaze upon acres of vineyards. doubles from $150.