When planning our Portugal road trip, the Alentejo – the region covering much of the south and east of the country – was top of our list. It has always been one of the most fascinating areas in Portugal for me. It is largely rural and remote, and gets very little of the tourist traffic that its southern neighbour the Algarve gets, but has some of the best places in Portugal to visit spread across the region.

As some of these are hours apart from each other, in areas where public transport is scarce, our only real option was to work out a Portugal road trip itinerary and shop around for car hire from Faro airport.

Image of cork trees in Alentejo region on road trip Portugal

Cork trees are a common sight in the rural Alentejo region

Much of the Alentejo landscape is agricultural, dominated by gentle rolling fields full of flowers, with groves of cork or olive trees and crumbling old farm buildings.

Yet Alentejo Portugal also has a long and fascinating history, going back to prehistoric times. We planned our Portugal itinerary so that we would explore some of the most beautiful towns in Portugal, and see some dramatic mountaintop border villages.

A Portugal Road Trip: What To Expect

Image of a narrow street in Marvao in the Alentejo region Portugal

“Are you sure we’re going to get down here?” A narrow street in Marvao

We have driven in several European countries, and the same road rules as everywhere else are applicable.

On the whole, we found driving in Portugal no different to anywhere else in Europe. Some people swear by satnav when travelling abroad. We have always gone with the one driver, one navigator set-up, with Faye driving and me reading the map and directing accordingly.

One of the best driving in Portugal tips to bear in mind is that some of the towns have very narrow medieval streets, built 700 years before the advent of the motor vehicle. We got by without any dints and dents, but it was sometimes a very tight squeeze.

Image of empty motorway, part of the experience of a tourist driving in Portugal

The wide open road: a typical view of a Portuguese motorway, with hardly another vehicle in sight

In Portugal road tolls apply on motorways and certain roads around Lisbon. We didn’t need to drive far on Portugal toll roads but found driving on motorways there to be very easy and fast. This is partly because people take alternative, toll-free routes if there are any available.

Most of our fellow motorists were fine, but we did encounter the occasional impatient and erratic driver on our travels. Swerving around to our left, overtaking us and then diving across us at 100 km an hour to take an exit to the right 200 metres further on is a manoeuvre you don’t encounter often. The middle-finger-toting granny who got irate at us for being unsure which roundabout exit to take – and then nearly veered off the road – is another who sticks in the mind.

Into Alentejo – Faro to Évora

Our route took us from Faro airport on the Algarve coast up through the country’s rural hinterland to the region’s capital Évora, where we stayed for three nights. We decided to fly into Faro because we wanted to spend a week in the Algarve after our road trip. However this road trip could just as easily have been done flying into and driving from Lisbon Portela airport, which we’ll cover later in the article.

We departed Faro in light rain, and as we headed north into the hills of inland Algarve, we had to stay cautious as a murky mist descended. However, not long after we crossed the provincial border into Alentejo, the sun emerged, and accompanied us for the rest of our journey. We were soon into the familiar Alentejan landscape, with its cork and olive groves everywhere we looked. We passed the village of Almodovar, eventually reaching Castro Verde, which is significant in Portuguese history as it’s close to the site of the Ourique battlefield where Afonso Henriques defeated the Moors in 1139, paving the way for his declaration as the first King of Portugal. The 18th century Basilica Real church in the town is well worth the detour to see its magnificent azulejo (tile) decorations, which cover the interior walls.

We had a choice of routes from Castro Verde to Evora, and opted for the slightly longer route up the E802, which passed Beja, the provincial capital, though we didn’t have time to stop there. The E802 continues past Vidigueira, joining the N256 for the final run into Evora.

Évora – Capital of the Alentejo, Portugal

Best road trip Portugal Image of Evora Sé or Cathedral at night

Evora’s Sé, or Cathedral, is at its most magical at night

Évora is one of the best cities in Portugal to visit. an ancient city with some incredible sights and the intimate feel of a small country town rather than a provincial capital. The old city is inscribed on the UNESCO World Heritage Site list.

It also presented us with our first logistical challenge, as we had somehow mislaid our printout of our map of the approach into the city. We went by the navigator’s nose, and found our way to the old city, where we were staying – just the wrong part, a minor detail we were soon able to rectify. We soon found our Évora accommodation, Pensao Policarpo, down a very narrow street with an equally tight entrance. After negotiating both Faye awarded herself a couple of days off the road, which I was more than happy to go along with.

Image of the Roman Temple of Diana Évora

The remarkable Roman Temple of Diana in Évora

We’ll be publishing a much more detailed feature on things to do in Évora in the near future, so won’t duplicate content and go into much detail here.

However, we will say that this is one very special city which totally captured our hearts. Our hotel room had one of the best views I’ve ever had – over rooftops to the spectacular Sé, or cathedral, which dominates the city skyline. We loved wandering the streets between our Evora hotel and the cathedral, and sitting outdoors at a table next to a kiosk across the road from the Roman Templo da Diana. We’ve yearned to be back there ever since.

Image of skulls in the Chapel of Bones in Évora

Skulls in the Chapel of Bones in Évora

Evora is one of the more popular destinations for day trips from Lisbon, which is under two hours away. A day doesn’t do Evora justice, it’s somewhere best savoured over two or three days, exploring the medina-like backstreets at night. However if that’s all the time you have it’s worth coming to see the sights we’ve mentioned, and the remarkable Capela dos Ossos, the Chapel of Bones, next to the church of Sao Francisco. The interior is decked out with skulls and various other bones – a grisly but compelling sight. The sign above the door says something to the effect of “We bones await your bones”. No wonder cremation’s so popular these days.

On to Estremoz and Marvao

Image of Saturday market at Estremoz, one of the best small towns in Portugal to visit

The Saturday market at Estremoz takes over most of the main Rossio square

We could have happily stayed in Evora for a few more days, and had a couple of drives out of town to some of the prehistoric sites nearby, including the Cromleque dos Almendres. We managed the tight squeeze out through the gate, bidding farewell to Evora and finding our way onto the E802 road heading north-east towards the border.

We had pencilled in a stop in Estremoz well before the trip because we knew we would be passing through on a Saturday, when a huge open air flea market is held in the Rossio, the town’s main square. It’s a huge occasion, drawing sellers and buyers from all over the Alentejo region and beyond.

En route to Estremoz, we saw the impressive castle and battlemented town walls of Evoramonte, but sadly didn’t have time to stop.

Estremoz is a fine town, much of it built from locally quarried marble. The Rossio is huge, and the market fills most of it. I’m used to Faye picking up all sorts of items at markets around Europe, and wondered what she’d find this time. I gently reminded her of Ryanair’s stringent baggage restrictions before wandering off to shoot some photographs.

Image of antiques sign in Portuguese at Estremoz market

Art Nouveau style antiques sign at Estremoz Market

Estremoz market is amazing. The flea market – with all kinds of antiques, old possessions and paraphernalia, is one of the best we’ve ever seen, and the food and farmers market across the square likewise. I came back from my walk wondering whether we had acquired any new furniture or small livestock, but Faye was more than happy with several boxes of vintage buttons.

Image of market stallholder at Estremoz Alentejo Portugal

A local character at the Saturday market in Estremoz

After a couple of hours around the market we stopped for lunch at a lovely little bar on the corner of the Rossio. The rest of the town, especially the citadel and castle, looked wonderful, and the Pousada Castelo de Estremoz is among the best luxury hotels in Portugal, with great views over the town and the plains of Alentejo.

Our next destination was Marvao, 75km to the north along the E802 followed by a cross-country short-cut.

Marvao, Portugal

Image of Marvao Castle, one of the best places to visit Portugal

The Castelo de Marvao, one of the best castles in Portugal

Marvao is one of most special places we’ve visited in Europe, a tiny whitewashed village straddling a precipitous narrow ridge in the Serra de Sao Mamede mountains, with outstanding views down from either side, and the Castelo de Marvao, one of the most impressive of all Portuguese castles. This remote mountain fastness looks impregnable, and indeed was never captured. It’s an amazing sight that would be a highlight of any Portugal trip.

After zig-zagging up the east of the mountain to reach the entrance to the village, we thought for a moment or two that Marvao might also be impregnable to hire cars – the cobbled streets were among the narrowest we’ve ever driven, and we didn’t think our humble little vehicle was going to make it through the archway, but we did, just about, with wing mirrors still attached and intact.

Image of traditional chimneys in Marvao Alentejo

Traditional chimneys on house in Marvao

Our Marvao accommodation was in a beautiful medieval house with a sublime view over the border to the vast western Spanish plain to the east. Several Marvao hotels are spread around the village, with the Marvao pousada occupying a commanding site on the western side, at the opposite end of the village to the Castle.

Image of Castle in Marvao Portugal

The Castelo de Marvao and formal gardens below

We made straight for Marvao Castle, an imposing sight above a pretty formal garden at the summit of the mountain on which the village is built. It’s a medieval masterpiece, its stout, solid walls built on cliff edges with sheer drops either side. You pass three sets of walls before entering the main body of the castle, which has great wall walks on both sides. The most impressive aspect is its location on such a high precipice, perched in dramatic border country. It’s a site that you can’t really appreciate from down below – you need to visit the Castle itself to get the full effect.

Image of village from Castle walls Marvao Alentejo Portugal

Marvao village at sunrise from the Castle walls

We chatted with the custodian on the way out, asking about access to the castle for sunrise. He tipped us off, telling us that the door wouldn’t be locked overnight so we were able to sneak in for an unforgettable sunrise the next day.

Apart from the castle, the village is fascinating to explore for a few hours, with amazing walks along the walls and the narrow cobbled streets. We found that one night in Marvao is probably enough, especially if you’re trying to cram in a lot as we were.

Castelo de Vide

Image of backstreets and castle at Castelo de Vide Alentejo Portugal

The gorgeous backstreets and castle at Castelo de Vide

The next morning, we squeezed our little car out through the cramped cobbled streets to resume our journey. We briefly detoured out into the countryside below Marvao to see a prehistoric site between the village and the Spanish border, before stopping by at Castelo de Vide (C. Vide on local road signs) for a quick coffee and supermarket shop to stock up on supplies before heading south towards the border citadel of Elvas for a few hours there.

Castelo de Vide is a small medieval town in north-east Alentejo, clustered around a castle on a hilltop, and much as we wanted to stop to explore, there just weren’t enough hours in the day. The coffee and accompanying pastry was delicious, and boosted by the sudden sugar and caffeine rush, we decided to have a quick walk down the hill to the Juderia, the Jewish district. Just for a few minutes.

Image of a sleeping cat in Castelo de Vide Portugal

A Castelo de Vide cat having a morning snooze

Three and a half hours later, after exploring many a tiny cobbled backstreet – many petering out into private courtyards – and gradually ascending the steep hill to the medieval castle, we made it back to the car, in the knowledge that we wouldn’t have time even for the most cursory glance at Elvas, which was very sad.

However, we made a wonderful discovery in Castelo de Vide. It’s a gorgeous whitewashed town, way, way off the tourist trail, and the longer we spent there, the more we were taken with it. It is a spa town, and you can sample some of the refreshing clear water in the Fonte da Vila, down in the Juderia. We slowly ambled up through the higgledy-piggledy backstreets, totally forgetting the time, probably because we felt we had stepped so far back in it. We passed and noted a couple of Castelo de Vide hotels, thinking that we must come back and stay there for a few days.

South to Elvas and Monsaraz

Image of the Amoreira aqueduct in Elvas Portugal

The mighty Amoreira Aqueduct in Elvas

We now had a long journey, running roughly parallel with the Spanish border, to our next destination, the mountain-top village of Monsaraz, which has recently been voted the most beautiful village in Portugal. This was going to be a largely backroads run, so we had to allow around four hours for the whole trip.

We joined the N246 just to the west of Castelo de Vide, heading south from the hilly Serra de Sao Mamede to the more typical Alentejan countryside we had seen the first few days of the trip, driving past flower-filled meadows dotted with partly-stripped cork oak trees.

At Santa Eulalia we opted to add the best part of an hour to our journey, taking the left fork instead of the right and heading to Elvas. As map reader I realized that one possible route passed right underneath the mighty Elvas aqueduct, and Faye agreed to the detour.

The massive Amoreira aqueduct (Aqueduto da Amoreira) was built in the 16th century to bring water to the fortified town. It runs for around 8 km (5 miles) from a spring to the west of the town, and it’s hugely impressive. We stopped just below it, with uninterrupted views across the park and valley. There were probably enough things to do in Elvas to stop for a couple of days, never mind a couple of hours – the old town, the star-shaped fortress – but painful as it was, we had to press on.

The journey was taking longer than anticipated, so we decided to abandon our original route down a minor road to Alandroal was going to take too long if we were going to reach Monsaraz before nightfall, so we would stick to the main roads for the rest of the way.

There’s always a plus side in situations like this – if you miss one thing, there’s a good chance you’ll see something else. The grand town of Vila Viçosa, home to the Palace of the Dukes of Bragança, was somewhere we didn’t plan on passing, but we got a good view of the town’s famous marble quarries from the road. Here was yet another discovery to be revisited in the future.

After this, we had a clear run down the N255 to the wine town of Reguengos de Monsaraz, before taking the M514 the last 15 kilometres (10 miles) or so to our final destination, Monsaraz.


Image of village street at dusk Monsaraz Portugal

The empty streets of Monsaraz at twilight

Monsaraz has just been voted the most beautiful village in Portugal.

This walled, whitewashed village and castle enjoys a magnificent setting, the scenery gentler, and less dramatic than that around Marvao. It’s outstanding all the same, with the Alentejo countryside to the west and the many lakes that make up the Barragem do Alqueva reservoir system to the east. It’s quite a trek to this remote spot, but the experience of spending a night there was, for us, one of the best things to do in Portugal.

From the walls of the Castelo de Monsaraz, at the southern end of the village, you have a glorious view of the Alentejo plain in one direction and the lakes in the other. The village is essentially two long streets, with a few narrow streets and alleyways connecting the two. The skyline of whitewashed towers, turrets and chimneys is stunning in the late evening light.

Image of Monsaraz Castle Monsaraz Alentejo Portugal

Monsaraz Castle and village at dusk

Monsaraz is a long way from anywhere else but has been fiercely fought over in the past, and at various times has been under the control of the Moors, the Knights Templar and the Earl of Cambridge, as well as the kingdom of Portugal.

We had arrived an hour before sunset and wandered the streets and alleyways until well after nightfall, by which time most Monsaraz restaurants had closed, so we were left sharing the streets with a few cats.

Monsaraz is also part of the Alqueva dark sky reserve. As the area is so sparely populated, light pollution levels are among the lowest in Europe, so the area is excellent for stargazing.

Image of Alqueva lakes from Monsaraz

The Barragem do Alqueva lakes from Monsaraz at sunrise

Our Monsaraz accommodation was in the Casa Rural Santo Condestavel, a beautiful townhouse on Rua Direita, close to the main square and church, with an amazing view out over the Alqueva lakes from the terrace to greet the next day.

Most hotels in Monsaraz walled village are small guest houses, all in lovely medieval buildings with outstanding views, some from rooftop terraces. You’ll also find a few Monsaraz hotels in the surrounding countryside, as well as holiday homes, apartments for rent and some Monsaraz farmstays.

The next morning, we went for a wonderful sunrise walk outside the village walls before breakfast at Condestavel, and a browse around a couple of souvenir shops and a great coffee near the main gateway to the village.

From Alentejo to Algarve

Image of the Fonte de Telheiro fountain near Monsaraz

The ornate Fonte de Telheiro, in a village just below Monsaraz

And so we set off on the last day of our Alentejo tour. Our plan was to drive parallel to the Guadiana river and Spanish border, eventually moving westwards towards the motorway (autostrada) that would lead us to the next stage of our trip, the Algarve.

Again, we opted for the most scenic route possible, even if at times we would feel we had left ourselves a lot to do. The drive down from Monsaraz and across the Barragem da Alqueva lakes was a pleasure, crossing the water and seeing tiny flower-covered islets scattered across the landscape. The N256 took us to the outskirts of Mourao, another beautiful medieval whitewashed town with a castle guarding against incursions from across the border. But time was short, we had to continue, with great reluctance. We were only halfway down the lakes.

A short while later we reached Moura, at the southern end of the lakes. Yet again, we would have loved to stop, but this would also have to wait until another time. Our sole objective was to remain on the N255 and continue south, which we duly did. At Serpa we joined the N265, which took us to the more mountainous country of the Parque Natural do Vale do Guadiana, before one final brief stop in the Alentejo region, at the enchanting medieval town of Mertola, on the banks of the Guadiana.

Image of town and castle Mertola Portugal

The beautiful town of Mertola and its Castelo

We quickly realised that our car wasn’t going to be able to get down some of the tangle of tight streets, so we extricated ourselves from possible difficulty and parked just outside the old town, around which we walked for half an hour. Along with Elvas, this is somewhere we would love to revisit at some point.

Instead, we had to bid farewell to those evocative groves of cork trees as we reached the A2 motorway south to the Algarve, where we spent the next week of our adventure in Portugal.

Of the regions we’ve visited so far in Portugal, Alentejo is probably up there with the very best. We’d heartily recommend a trip to the Alentejo.  Monsaraz and Marvao are among the best villages in Portugal, and Evora is one of the most underrated cities in Europe. Then there are all the places we had to leave – it is an amazing region with so much to see, and one that deserves a minimum of a week of your time. Most of it is a long way off the regular tourist trail, and it often seemed that we were the only visitors in town.

And we didn’t even get near the Alentejo coast this time either.

Car Rental in Portugal

We flew into Faro, the airport for the Algarve region, which is very well served by airlines from all over Europe, including the various budget airlines (easyjet, Ryanair). We found some very good deals on car rental from Faro airport, and it also has easy access to the main roads in the area.

If you’re flying into Portugal from the US, Canada or Brazil, you would fly into Lisbon, which we’d recommend visiting before embarking on your road trip.  You can currently fly direct to Lisbon from New York, Boston, Philadelphia and Miami. Car rental from Lisbon airport is the most convenient option, as there are more options to choose from and it saves you having to negotiate traffic in the city itself.