In recent years, the Alentejo has captured the world’s attention—an agricultural region that people like to compare to Tuscany, with dusty wide-open landscapes under epic skies that some have likened to African savannas. It’s also rich in history, and home to some of Portugal’s best wines and gastronomy.

If I’ve learned one thing from my years of living in Portugal, it’s that if you go 20 miles in any direction, you will probably find something wonderful. And different from that other wonderful thing 20 miles away. (I like to say that Portugal is small but dense.) The Alentejo—the country’s largest geographical region and its least densely populated one—is no exception. So this isn’t definitive, by any stretch, but it hits some of the highlights.

Fitapreta

“My father is a chemistry professor and my mother is a historian,” says António Maçanita, one of the most interesting young winemakers in Portugal right now. “I work where history and science interlink. I see how wine was made many years ago and then do that in a more intelligent way.” That means recovering near-forgotten indigenous grapes, reviving traditional techniques and (sometimes) aging in amphoras. The result is wines that don’t taste like “Alentejo wines” but in fact have a closer connection to their place than much of what you find now. His Fitapreta winery occupies a medieval palace, parts of which date from the 14th century. (This really does look like something out of Tuscany.) The wine tourism operation is overseen by his wife, Alexandra, who has an event planning background. Sometimes there are special evening concerts, but even a simple lunch in the courtyard is deeply memorable.

Évora

The regional capital, Évora is a whitewashed city that’s layered with history. The massive Gothic cathedral was begun in the 12th century, and the Igreja de São Francisco and haunting Chapel of Bones dates from that same era. But much of the city is even older—in the historic center, there’s the ancient Roman Temple of Évora, also called the Temple of Diana. The floor in the town hall is partly glass, so visitors can admire the ruins beneath, and Roman remnants are so prevalent all over the city that some locals are reluctant to renovate their homes, for fear of turning up something else that needs to be preserved. Shortly after I left, a food-loving friend asked me where I had eaten—Évora (about 90 minutes from Lisbon), it turns out, has become a day trip destination for its blooming restaurant scene, including Tua Madre, Híbrido and Taberna Santo Humberto. They’re top of my list for next time.

Convento do Espinheiro

Just outside of Évora, this historic hotel occupies a 15th-century convent that over the years was regularly visited by Portuguese monarchs, who expressed their devotion to Our Lady of Espinheiro (thorn-bush, where an apparition of the Virgin Mary is said to have appeared) by leaving behind lavish gifts. The result is a 90-room convent hotel of unusual opulence and comfort. The restaurant is also worth a visit, as chef Jorge Peças uses local ingredients including olive oil, meat and fresh herbs produced on the property.

Estremoz Saturday Market

On Saturday mornings, people from all over the region gather on one of the central squares of Estremoz, another whitewashed village with a deep history and a whole lot of marble (which is quarried all around here). Along with vegetables from local farms, a dizzying array of local sausages and cheeses, there’s also a market for antiques, household goods and pottery.

Mercearia Gadanha

While traditional Alentejo gastronomy—lots of meats and hearty dishes that used to fuel the farmers—is often very satisfying, that’s not what’s on offer at Mercearia Gadanha. In the center of Estremoz, a shop and wine cellar sell top-quality local products, while chef Michele Marques’s restaurant in the back turns out unusual and surprising fare with traditional ingredients. Something listed on the menu as “fantastic soup” turned out to be just that: tomato-strawberry gazpacho with sweet prawns and basil granita. The dishes that followed were no less delicious.

Museu Berardo Estremoz

Opened last year and still under the radar, this museum in the historic Tocha Palace is a collaboration between one of the country’s largest private collectors and the city government. The inaugural exhibition follows 800 years of the gorgeous Portuguese tiles called azulejos, from their geometrical origins in the Islamic world to 20th-century advertising (as well as the late-Baroque and Rococo tiles in the palace itself), and features the largest private collection of tiles in the country.

Torre de Palma Wine Hotel

Deep in the countryside, this family-owned hotel became the first five-star property in the region when it opened in 2014. It’s centered on a tower from 1338 but decorated with colorful, contemporary furnishings and many antiques that belonged to the mother of one of the owners (who was born in this area but lived far away most of her life), which have been painted white to give them a more up-to-date look. They also produce some top-notch wines (and offer top-notch wine-tourism experiences, particularly around the harvest) and have a great restaurant. Chef Miguel Laffan, who held a Michelin star at a previous restaurant, recently signed on as a consultant, and the menu has artful renditions of classic Alentejo dishes, like roast-duck pastries and black pork with cornbread and asparagus.

Source: Forbes