East of Lisbon, the Alentejo is emerging as a world-class wine destination. From artisanal markets to hilltop tavernas, Raymond Sokolov uncovers the region's best.
David Nicolas

Portugal is the last major European country to have entered the modern world. Some thirty years ago, an astute man I know predicted this belated debut and bought up every share he could on the Lisbon exchange. Then he waited until the Salazar dictatorship fell, at which point he became very rich. Yet even 10 years ago, people in Madrid who heard I was going to Lisbon said it would be "the way Madrid used to be."

And it was, although the ATM's were already there. Today in Lisbon, you can eat in a trendy place owned by John Malkovich; television is so unfettered that people find it kinky when the actors on the late-night shows wear clothes; 1998's Lisbon Expo Disneyfied the waterfront. And a short drive out of town, on excellent roads built with European Union funds, the old Portugal of oxcarts and sleepy villages is still there, holding on to its soul but eager to meet the rest of the world halfway.

I am racing east on one of those roads into the mountainous Alentejo region, which ought to mean boondocks but actually translates as "beyond the Tagus," the river that spills into the Atlantic and gives Lisbon its majestic setting.

From Lisbon's airport, built for the Expo, it takes five minutes in a rented Fiat Punto super-mini to reach the sail-like cables of the Vasco da Gama bridge, which leads smoothly over the water. My quest has begun. On my first visit to eastern Portugal, in 1994, mule carts and peasant women in black were the main sights, along with deserted castles and cork oaks. I've now returned with my wife, a globe-trotting sculpture curator, to confirm enticing reports that this former backwater has brightened up with stylish hotels, adroit presentations of regional foods, and cheeses tuned up for export. Most of all, I'm here to witness the remarkable evolution of the area's wineries, a process that has transformed the murky plonk that most Americans associate with Portuguese wine into a distinctive—and often pricey— competitor for the fussy wine-bibber's attention.

The oaks are still here, darkly punctuating the wheat fields. The single-digit numbers painted on their stripped, smooth, reddish trunks stand for the year their bark was last peeled away and converted into bottle stoppers. By law, the process can be repeated every nine years, ensuring Portugal's supremacy as the world's leading cork producer. This may not be a cause for rejoicing much longer, as even first-class wineries from Sicily to Sonoma are converting to synthetic corks and metal caps. But it makes for a lovely landscape of widely separated big old trees with thick green foliage and large acorns, flocks of sheep and cattle, and not much else. After about an hour and a half of bucolic high-speed travel, we exit at Estremoz ( pronounced "shtre-moj"), one of the hubs of the new Alentejan wine scene. The tourist office is closed, but a sporty woman emerging from an SUV directs us through an unmarked single-lane break in the ramparts toward our hotel.

We could have booked a room in the swank, air-conditioned pousada that occupies the 14th-century castle (complete with crenellated towers) perched on the acropolis above Estremoz. But we're looking to break away from the beaten path of globalized five-star lodgings that Portugal's network of pousadas epitomizes. And we got a convincing tip from a discriminating friend that we'd find what we sought at the Convento de São Paulo, a 17-mile drive away along a lush winding road, in the tiny village of Aldeia da Serra (Mountainville).

The former monastery looms massively against a wooded slope and overlooks a green, deserted valley. Among its seductions are cloistered gardens, a Baroque chapel, a circular swimming pool, forest hiking trails, and a dining room expertly faithful to Alentejan specialties—gutsy thick soups and pork in every form, including deboned trotter with garlic and fresh coriander (coentro), served in emphatic quantities—and alert to the newly sophisticated local wines. But none of these estimable advantages are the reason a couple of jaded sybarites like my wife and me would tout the Convento as one of the most remarkable places we've ever spent the night. Nor is it the casual service provided by cheerful locals, or the sunlit cloister : it's the tiles that have won our hearts.

Everywhere you turn in this place, you pass murals made of blue-and-white glazed Baroque tiles—more than 54,000 of them, the hotel claims. Once you start looking at the religious and historical scenes on the murals lining Convento's long, kerosene lamp–lit halls, it is hard to clip along efficiently to your spacious renovated monk's cell with its views of the valley and the gardens below. I'd happily spend a rainy day gazing at these martyred saints and knights as they ride forth to win greater glory for some forgotten Portuguese ruler. The true aesthete could stay all day at the Convento, but we must begin our expeditions.

We start at the famous Saturday market in the praça, or central square, of Estremoz. Surrounded by a former palace and a Baroque church, crowds fill shopping bags with everything from red-clay pottery to live chickens and rabbits. We gravitate toward the cheese stalls, really just simple tables covered with small rounds made of goat's, sheep's, and cow's milk and blends of the three (mistura). These are basic farmhouse cheeses, some fresh, some aged. Many bear monochromatic labels printed with the name of the dairy and the variety. Even at this grassroots level, the movement to standardize Portuguese cheese s is taking hold. Some of the better-known types, all made with sheep's milk— Serpa, orange from being rubbed with paprika and oil, spiky Beja, and creamy, fresh Évora—are already finding their way to restaurants in New York. (When I got back to Manhattan, I was amused to see a city magazine praising the restaurant Artisanal for carrying Serpa and Serra, another prized Portuguese sheep's-milk cheese.) In the Estremoz market, a French foodie buzzword is also in vogue, on homespun labels that read QUEIJO ARTESANAL.

Back on the road, we start noticing signs marking the Rota dos Vinhos do Alentejo, or Alentejo Wine Route. This is a regionwide association of vineyards ostensibly open to the public, often with tasting rooms (adegas) in their white-walled, red-tile-roofed wineries. I say "ostensibly" because, upon closer inspection of the fine print in the brochure and on the route's Web site, it becomes clear that the vintners insist on appointments. Even the most glamorous vineyards, like Quinta do Carmo, near Estremoz, are basically fruit farms, not theme parks. And when you locate the center of Reguengos de Monsaraz on the map, you won't have an easy time finding the renowned restaurant and tasting facility for Herdade do Esporão, which produces a wide range of "modern" wines. But we manage, and it's worth the hunt: the Esporão Reserva is a complex and intelligent blend of native and Cabernet Sauvignon grapes. Though drinkable now, it has a tannic structure clearly intended for Bordeaux-like mellowing with age. The vineyard's adjoining restaurant is known throughout the region, and reservations for a lunch of duck salad and red wine are essential on weekends.

Sure enough, we can't get a table there, so we head for Évora, a romantic regional center, for a late lunch at the venerable Fialho, a self-styled cervejaria, or beer hall. Fialho is not only Évora's most celebrated restaurant but also one of the most revered in all of Portugal. This does not translate into fussy cooking or standoffish service. Quite the contrary—the atmosphere is that of a family tavern, although the staff remains professional and polished. Fialho is where you will find a homely-sounding dish like pork and clams, the region's specialty, raised to its highest level, a sensuous mix of rich, tender meat and ascetic, chewy shellfish.

Back in our monk's cell at the Convento, we collapse on our four-poster, resting up for another adega, near Sousel, just a bit north of Estremoz. More picturesque and quirky than Esporão, the Herdade do Mouchão, a family-run estate established in 1901, is a deliberate anachronism. The owners, Ian and Emily Richardson, make wine as if electricity and modern oenological advances had never blemished God's green earth. This is the place to go to sample authentic heavy vinifications of native Alentejo grapes, such as Trincadeira or Aragonês. Elsewhere in the high Alentejo, however, stainless-steel vats have replaced their wooden predecessors, and oenologists from Australia, France, and California's Napa Valley are transforming wines dramatically, and for the better. An infiltration of methods and grape varieties similar to those that revolutionized sleepy vineyards in Tuscany and southwestern France is turning around a region proverbially known as the "land of bread and bad wine." There is still plenty of $5 paint thinner in the bottle shops, but a quick scan of wine lists in restaurants reveals the change taking place. You pay globalized prices for these spiffy newcomers, of course— $30 to $40 for labels you have probably never heard of.

That's about what we pay for a superlative red Esporão '99 at the Luar de Janeiro bistro in Évora, which drew us in with its display of high-end local wines at the door—a good sign. As are the appetizers, especially the mushrooms in oil and mint, the oil swelling the mushrooms with unction, the mint adding its tang as a grace note. But all of this is merely a prelude to the extraordinary cabrito, kid roasted brown and crisp, cut in many pieces from the leg and shoulder but still on the bone. If this is Alentejan peasant cooking, I want to sign up for a job on a quinta, one of the big landholdings that survived the antifascist revolution of 1974.

Perhaps the cushiest of these estates is Quinta do Carmo, where every vine looks as well tended as a bonsai. The property, which dates from the 17th century, is now in partnership with the Rothschilds of Château Lafite. The reserve is roughly 75 percent local grapes, with Cabernet and Syrah accounting for as much as 40 percent. This is a big wine that will stand up to Alentejan food—or a juicy American steak. Without an appointment at the vineyard, we resign ourselves to tasting the wine over lunch at the Pousada Rainha Santa Isabel in Estremoz on our last day in the Alentejo. We are once again reminded that one of the best—not to mention most convenient—ways to sample the new Portuguese vintages is at local restaurants, where they pair effortlessly with the rich cuisine of the region.

Such is our luck that we manage to dine on our last night at Tasquinha d'Oliveira, an excellent small tavern in Évora. Owners Manuel and Carolina d'Oliveira follow the local custom of beginning the meal with a couvert. This is not just a descendant of the bad old European restaurant gimmick of charging for the bread and the place setting (couvert in French). In the Alentejo, couvert indicates an hors d'oeuvre not on the menu. Tasquinha serves 10 small plates—salads of roasted pimientos, rabbit, octopus; a sort of chicken quiche; breaded lamb riblets; goat cheese with quince paste—all of them delicious. We try some of each, not understanding that we're expected to choose one or two and send away the rest. The waiter, unfazed, lets us nibble freely—then charges us for everything we have touched.

The main courses are hearty, even sumptuous. I order the ancestral migas à Alentejana: tender little spareribs tucked into the coarse-grained local version of polenta. My wife orders a mildly gamy braised hare with white beans. This may sound like home cooking, and it is certainly sturdy fare, but it's presented with three-star panache, and the ingredients are brilliantly fresh. We round out the meal with a memorable Adega de Pegões, red, light, and as seductively bouqueted as a fine Burgundy.

To recover, we coax the Punto to take us a few miles out of town to a clearing in a cork oak grove, where we see the cromeleque dos almendres (cromlech of the almond grove), a neolithic stone circle. Here is Old Europe going strong. And if we'd had our wits about us, we would have brought a bottle of Quinta do Carmo Reserva, to toast the Alentejo's new take on its long and rich heritage.

RAYMOND SOKOLOV, a former editor at the Wall Street Journal, is the author of The Cook's Canon.

Alentejo's Wine Route is about as modern as the medieval villages it passes through, so visiting the wineries can be a challenge. Be sure to call ahead for appointments. Two of the more dependable vineyards are Herdade do Esporão (Reguengos de Monsaraz; 351-266/509-280; www.esporao.com), where you should try the acclaimed Reserva, and Adega da Cartuxa (Évora; 351-266/748-380; www.jpvinhos.com), which has a wide selection of wines not available in the United States. Quinta do Carmo (Estremoz; 351-268/337-320; www.lafite.com), known for its reds, also offers tours. The Alentejan Wine Route association has maps and information on other area vineyards (351-266/746-609; www.vinhosdoalentejo.pt). Or let a tour company make the arrangements for you. The excellent Madrid-based Cellar Tours (34/91-521-3939; www.cellartours.com; two-day tours from $2,060) can get you into hard-to-visit boutique wineries such as Tapada dos Coelheiros and Herdade do Mouchão. One not-to-miss stop is the Vinhos Alentejanos wineshop (351-96/700-3631) in Évora. Ask owner Antonio de Sousa for Cortes de Cima's Incógnito and Reserva; Quinta do Carmo's pedigreed red; and Francisco Nunes Garcia's "Aragonês Alentejo."
—Anthony Giglio

Convento de São Paulo
Don't miss the hotel's excellent restaurant, O Ermita. Aldeia da Serra, Redondo; 351-266/989-160; www.hotelconventospaulo.com; doubles from $250.

16 Travessa dos Mascarenhas, Évora; 351-266/703-079; dinner for two $85.

Tasquinha d'Oliveira
45A Cândido dos Reis, Évora; 351-266/744-841; dinner for two $90.

Pousada Rainha
Santa Isabel Largo Dom Dinis, Estremoz; 351-268/332-075; www.pousadas.pt; dinner for two $100.

Luar de Janeiro
Closed on Thursdays. 13 Travessa do Janeiro, Évora; 351-266/749-114; dinner for two $70.

Herdade do Esporão
Book in advance. Lunch includes a wine tasting; dinner available only to groups of 10 or more. 31 Apartado, Reguengos de Monsaraz; 351-266/509-280; www.esporao.com; lunch for two $110.

Quinta do Carmo

Adega da Cartuxa

Herdade do Esporão

Herdade do Esporão Restaurant

Luar de Janeiro

Pousada Rainha Santa Isabel


Convento de São Paulo