In His Insider Guide To Alentejo, Rupert Parker Discovers One Of Portugal’s Hidden Gems.
Stretching from the banks of the Tagus River down to the rugged cliffs of the southwestern coast, Alentejo covers nearly a third of Portugal’s landmass, yet it remains one of Europe’s least populated regions.
The first thing that strikes you is the space – vast, sun-drenched fields of wheat and wildflowers that roll toward distant olive groves. Scattered across the plains are clusters of cork oaks, their trunks scarred from harvest, symbols of an ancient rural economy that still sustains local life.
There’s a quiet rhythm to Alentejo – a pulse that beats slower than the rest of Portugal. Travelers often rush past on their way from Lisbon to the Algarve, but those who pause here soon discover that Alentejo is not a region to be hurried through – it’s a place to be felt, savoured, and remembered.
It’s also one of Portugal’s most important wine regions, producing full-bodied reds and surprisingly elegant whites. Visit a winery such as Fita Preta near Evora or Herdade dos Grous near Beja, which also has livestock and olive trees. Wine tastings here often come with olive oil samplings, cured meats, and the kind of conversation that lasts well into the afternoon.
Évora
At the heart of Alentejo lies Évora, a UNESCO World Heritage city that feels like an open-air museum of Portuguese history. Surrounded by medieval walls, Évora’s cobblestone lanes twist through centuries of architecture – Roman temples, Moorish courtyards, Gothic cathedrals, and whitewashed townhouses adorned with azulejos tiles.
At its heart stands the Praça do Giraldo, Évora’s main square. Once the site of executions during the Inquisition, it now hums with café chatter and the scent of strong Portuguese espresso. The square’s arcaded buildings glow in soft limestone hues, while a 16th-century fountain, topped with a cross, keeps watch over the city’s comings and goings.
Perched on a small hill overlooking the old town is the Templo Romano, its tall Corinthian columns, carved from granite and capped with marble, rise against the Alentejo sky. This ancient monument, dating from the 1st century AD, survived invasions, earthquakes, and even centuries of neglect – thanks, ironically, to being incorporated into a medieval slaughterhouse.
Just steps away, the eerie Capela dos Ossos (“Chapel of Bones”) offers a haunting reminder of mortality – its walls lined with thousands of human skulls and bones. Hidden inside the Church of São Francisco, this macabre masterpiece was built by Franciscan monks in the 16th century as a meditation on mortality. Above the entrance, a chilling inscription reads: “We bones that are here, await yours.”
Monsaraz
Beyond Évora, the countryside unfolds into a patchwork of sleepy villages, each one a postcard of whitewashed houses trimmed with cobalt-blue or mustard-yellow paint. Monsaraz, perched high above the Guadiana River near the Spanish border, is among the most enchanting.
Inside its medieval walls, cobblestone alleys wind past craft shops and tiny taverns, all overlooking the glittering waters of the Alqueva Reservoir, Europe’s largest artificial lake. At night, Monsaraz becomes a stargazer’s paradise, part of the Dark Sky Alqueva Reserve, one of the world’s first certified starlight tourism destinations.
Beja
Beja is the capital of Lower Alentejo and its story begins long before Portugal existed as a nation. Founded by the Romans as Pax Julia in the first century BC, it was named to commemorate peace between Julius Caesar and local tribes. The city later passed through the hands of the Visigoths and Moors, each leaving traces in its architecture and culture. Narrow lanes winding past whitewashed houses, adorned with wrought-iron balconies and bursts of bougainvillea.
At the heart of Beja stands the Castelo de Beja, whose imposing keep rises proudly above the city. Built in the 13th century under King Dinis, the tower is one of Portugal’s finest examples of Gothic military architecture. Climb its spiral staircase to the top, and you’re rewarded with sweeping views of the Alentejo plain. Below, red-tiled roofs cluster around cobbled streets, while the white spire of the cathedral glimmers in the sunlight.
Next to the castle lies the Museu Regional de Beja, housed in the former Convento de Nossa Senhora da Conceição, a 15th-century convent of serene beauty. Its cloisters, lined with blue-and-white azulejos (tiles), whisper of quiet devotion. The museum’s treasures include Roman artefacts, sacred art, and delicate Moorish ceramics. But its most famous relics are the “Letters of a Portuguese Nun”, passionate love letters written in the 17th century by a young nun, Mariana Alcoforado, to a French officer.
VINIPAX
I time my visit to Beja to coincide with VINIPAX, the wine fair that brings together the southern Portuguese wine world in one lively venue. For three days, in October, the city becomes the heart of Iberian wine culture, offering tastings, workshops, and authentic Alentejo food.
This year, some 40 exhibitors and around 60 producers from Portugal and Spain are present with more than 350 wines to be tasted. What this means for visitors is a rich palette of styles: from luscious, generously-fruited Alentejo reds and warm, golden whites, to sharper, mineral-tinged Trás-os-Montes wines. It’s an excellent opportunity for both seasoned wine-lovers and the curious.
And there’s also food. A large section called “Sul à Mesa” (“South at the Table”) highlights regional cuisine. Local chefs prepare dishes like porco preto (black pork), açorda alentejana (bread soup with garlic and coriander), and migas (fried breadcrumbs with pork). Small tasting portions pair beautifully with the wines. For something sweet, try sericaia (a soft cinnamon custard) with a splash of fortified Moscatel.
By late afternoon, the fairgrounds come alive with live music and laughter. Groups of men burst into Cante Alentejano – the slow polyphonic singing that’s unique to the region. And it’s not just the singers who are fuelled by red wine, everywhere there’s the sound of chinking glasses. And that’s the magic of VINIPAX – it feels more like a village festival than a trade fair.
Tell Me More About Insider Guide To Alentejo, Portugal
TAP Air Portugal flies direct to Lisbon from London Gatwick.
The Gatwick Express is the fastest way to the airport from central London.
Vinipax happens every autumn in Beja.
Visit Alentejo has information about the region.
Visit Portugal has information about the country.
Mar de Ar Aqueduto is a historic hotel in a beautiful colonial building in Evora.
Forno de Telha serves refined cuisine in Evora.
Adega 25 de Abril in Beja has excellent traditional dishes from Alentejo.
Herdade dos Grous is a winery that offers tasting and good food near Beja.
Fita Preta Winery offers tastings and fine cuisine near Evora.
