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Portugal's Wine Region

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.

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