On Location: A Day in the Alentejo

Portugal’s Quiet Alternative to Umbria or Tuscany.

On Location: A Day in the Alentejo

By Gray Shealy


Elvas, Monsaraz, Borba, Estremoz, Evora—the stunning, fortified hilltop towns of Portugal’s Alentejo—dot toasted, rolling lands of golden grasses, olive groves, and neatly combed vineyards along the eastern Spanish border. It was hot: 105 degrees (F) to be precise, but the high ceilings and thick stone walls of the local architecture kept us cool while we were mesmerized by this extraordinary landscape. We visited wineries, markets, former palaces, castles, and strolled cobbled streets. The Alentejo is Portugal’s quiet alternative to places like Umbria or Tuscany.

We were house-hunting mid-pandemic. We had come to renovate something, and these were our first tours of real estate in Portugal. First up: a 20,000 square foot former hunting lodge from a 15th Century king of Spain. Frescos adorned the vaulted ceilings of ballrooms. Next up, an estate with crenellations and lovely gardens, but rotting stairs. It was all overwhelming. But, it put us squarely in the middle of towns we adored. Reguengos de Monsaraz was an ordinary village, but whose surroundings (wineries, fortresses, hot air balloons, lakes) made us yearn to explore more. We fell in love with nearby Elvas, on the Spanish border. It was also quiet, but had small streets to wander and a handful of museums and good restaurants to make it the perfect, off-the-beaten-path town, just far enough from the tourist trail to be really appealing.

In our few days, we town-hopped. We dreamed of the antiques on display in Estremoz’s Saturday morning market. We braved the tourist traffic in the university town of Evora, and relished a glass of wine in the nearby Cartuxa vineyard afterward. But, we found ourselves returning to Elvas again, wanting to get lost in the meandering streets, finding hidden cafes with views outward into the seared, Alentejo landscape. We didn’t end up with a fixer-upper (nor a former royal estate) there, but we will return when a vacation of solitude is called for.

Stay: Casa do Terreiro do Poço, Borba

See: Esporão Winery, Reguengos de Monsaraz and Cartuxa, Evora

Eat: Restaurante Acontece, Elvas

Photo Credit: Syllogi


Syllogi’s ‘On Location’ is a series of trip reports reflecting on our personal travels, as we research and experience the bounty the world has on offer.