Just over an hour’s drive from Lisbon lies the cobblestoned town of Évora, a UNESCO World Heritage site where Roman temple ruins, medieval streets and white houses checkered with azulejos tell stories of the city’s layered past. The capital of the Alentejo region and European Capital of Culture in 2027 is small enough to explore on foot, so plan to visit adjacent towns and attractions during your stay. It’s worthwhile to plot out an itinerary in advance: Many of the best spots are tucked away behind stone walls and inconspicuous facades.

Morning

Take in the morning sun with breakfast on the patio at Do Largo, a laid-back spot in the centre of town. The salty-and-sweet menu has options ranging from fresh-baked chocolate and hazelnut croissants to granola açaí bowls to cured salmon, plus fresh-pressed juices and lattes.

Next, pay a visit to the morbid yet mystifying Capela dos Ossos (Chapel of Bones). Set within the Church of St. Francis, the walls of this small 17th-century chapel are lined with the skulls and bones of some 5,000 people, displayed as a poignant reminder of the transience of life.

Reset with a leisurely stroll through the Jardim Público de Évora. With its old trees, moss-covered ruins and resident peacocks, the public garden offers a refreshing slice of life. From here, a short walk brings you to Évora Cathedral, the largest medieval cathedral in Portugal. Climb the 135-step spiral staircase to the rooftop for panoramic views of the city and the surrounding Alentejo plains.

Portugal is known for its ceramics and cork crafts, and there are plenty to be found in Évora. Head to O Cesto Artesanato, a charming shop filled with both traditional and modern ceramic dishware, along with home decor items like handmade wool throw blankets and cork fruit bowls. Each piece reflects the Alentejo region, making for a perfect souvenir.

From there, pop into the Rota dos Vinhos do Alentejo, a newly renovated wine hub installed to promote the Alentejo Wine Route (with guides who seem to know every winemaker in the region).

Afternoon

Set off to explore the surrounding countryside with a drive among fields of cork trees – a hallmark of the landscape – to Herdade das Servas winery. The journey itself is a treat, from the rolling hills to the cypress trees lining the estate’s driveway.

Lunch at the winery’s Legacy restaurant is a feast for the senses, with sweeping vineyard views on one side and an open kitchen busy with chefs assembling artful dishes on the other. Try the bacalhau à brás (salt cod and potatoes), a traditional Portuguese dish with a modern twist: molecular and freeze-dried olives.

The nearby fortified medieval town of Estremoz is worth a visit for the Museu Berardo Estremoz. In the 14th-century white palace, which overlooks the town’s public park, rooms spread over three floors showcase azulejo tiles in every colour, style and pattern imaginable, forming a collection from Portugal and abroad that spans more than 800 years.

When shops reopen after their midday break around 3 p.m., stop by Casbablanca Deco, a chic boutique with a selection of embroidered cushions, vintage lamps, handwoven baskets and restored furniture pieces. A treasure trove for thrift finds, Patine is filled with vintage tableware, prints, figurines and more.

Evening

Head back to Évora to catch the sunset from a courtyard table at top-rated Cavalariça. Set in a restored stable, this stylish restaurant is all good vibes, from its soulful playlist (listen for tunes by Cabo Verdean icon Cesária Évora) to friendly waitstaff who enthusiastically describe dishes like Alentejan pork with apple and smoked parsnip.

Photos cannot do justice to the picturesque Convento do Espinheiro, a 15th-century convent-turned-luxury hotel set among fields dotted with grazing cows, giant cacti and sprawling cork trees. Every corner of the building merits exploration, from the ornate on-site chapel to the marble-clad wine cellar (where guests can indulge in complimentary tastings). The crown jewel? The hotel’s Divinus restaurant, where regional specialties and Alentejan wine pairings are served within ancient stone walls under vaulted ceilings in a space once used by monks as nothing more than a wine and olive oil storage cellar.