ALENTEJO, PORTUGAL–The sun catches a row of whitewashed walls on a distant hilltop. In the overcast, that unlikely glint catches my eye and then a road sign confirms the point: We’re not lost.

We’d left on this day trip on the advice of our hosts in the old city of Évora. That town is a UNESCO world heritage site for its Roman ruins, but the couple insisted we had to visit Monsaraz.

It’s better, they said.

So, Meaghan and I drove east towards a town called Reguengos de Monsaraz. We stopped there. It was full of graffiti and pottery stores. I failed to get a signal for the GPS and we left confused. “That can’t have been it,” she said.

After that, I lead us on blindly. She grew increasingly frustrated that I’d left the map behind. We passed vineyards and a monastery and then that road sign.

Approaching from the west, the fort of Monsaraz rises like a fluke out of the flatlands of Alentejo. I wind our little rental car around behind the hill and hike the car up a switchback to the village’s east gate. I hesitate on the clutch at a frighteningly narrow ramp. We crest it, park alone in the cobbled lot near cherry trees just blooming and we laugh.

In late February, Portugal is full of incredulous laughs. On this trip – a mostly unplanned affair – we’ve laughed at the coastal cliffs and beaches in the south, the sunny weather, the silly-beautiful mountain roads and the wine. We’ve laughed in surprise; that a place like this would ever be so empty of anyone else like us.

Below some 400 feet and endlessly east the view goes on and on over the green valley of the Guadiana River into Spain.

The border is Portugal’s interior coastline. In the 13th century, Spanish knights coveted the region and the castle at Monsaraz took watch at the edge of the valley like a seabird on a cliff.

Today, the river is dammed and the valley flooded. The resulting reservoir is a superbly tangled lake. Back home, it would rival Muskoka for cottages. From our vantage it is a dreamy no-man’s land.

We climb the steps to the centre of the village. Even in the main plaza, Monsaraz is narrow; for foot traffic only and our feet only.

She and I walk atop the western wall. We pass a house that has collapsed recently. Its exterior wall melted out from under the clay-tile roof. Inside, we see a kitchen with blue walls boasting a new-looking dishwasher and stove.

I take photographs of the countryside through a washing line. Behind the flapping towels the view back west towards Reguengos de Monsaraz is in miniature like tilt-shift photography.

Alentejo is a landscape of vineyards. Lately, writers have taken to calling it Iberia's Tuscany. It is both one of the oldest wine growing regions in Europe and one of Portugal's youngest.

There are wines here from Roman times. Excepting the latter years of Muslim rule, local farmers sustained a winemaking tradition more or less continuously from the 1st century A.D. to the modern day. But, in the 1930s, Portugal's dictator Salazar forced the locals to tear up their vines to protect the Port producing Douro region to the north.

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Alentejan farmers grew wheat instead, even though it was a tragic waste of the dry sun and perfect harsh red soils.

It’s only in the last 20 years or so that the local wines have regained their quality. Popular cafes across the country overflow with excellent blends of local varieties: Arinto, Roupeiro and Antão Vaz the whites; Moreto, Alfrocheiro and Castelão the reds.

We sit for coffee and eat oily baked salt cod from a terrace looking out on the panorama. After eating, we buy a colourful pitcher and vase from a potter next door. She explains, in fine English, that she was a teacher in Lisbon before coming back here after the recession hit.

She paints a deft pattern on an unglazed plate. “It is sleepy here,” she says. “Even in the summer it’s quiet.”

Before leaving Monsaraz for good, I slough our tiny Citroën over rocks on a dirt path to a neolithic monument. I line up a picture of the menhir in the evening light.

In Alentejo, it’s easy to stumble on 6,000 year old stone circles sitting lonely like this amid cork plantations. Conceivably, we could spend a full day touring standing stones without meeting another foreigner.

But the light is gone and we haven’t planned for that. It starts to rain lightly, I return to the car and we laugh.

Just the Facts

Ed Tubb is a Toronto-based writer. Follow him: @EdTubb.

SLEEPING: There are a handful of AirBnB.com rentals in Monsaraz at around $100 CAD a night with a three day minimum, but nearby Évora makes a better base for a stay that long. The central town--itself a UNESCO world heritage site--also has more traditional hotels.

EATING: Portugal’s food culture is unsophisticated, but Xeraz Cafe Restaurante in Monsaraz pairs a nice local menu with an otherworldly patio. Order a simple stew and watch the sunset with a bottle of Alentejan red. For the budget minded, there’s no shame in stopping anywhere for some ubiquitous (and excellent) BBQ chicken.

HOURS: Be sure to plan for very un-Canadian restaurant hours. Some of the best restaurants in Alentejo open at lunchtime and close around 4pm, leaving unaware tourists to choose from sub-par options.