Portugal Tours Alentejo Image of Monsaraz village from castle ramparts

Portugal Road Trip Alentejo Guide- Beautiful towns & Mountaintop Villages

Planning a road trip through the Alentejo region in Portugal? Here’s my Portugal Road trip Alentejo guide. Discover the Alentejo region, its beautiful capital Evora and stunning mountaintop castles on one of the best road trips in Portugal.

When planning our Portugal road trip Alentejo – the region covering much of the south and east of the country – was top of our list. It had always fascinated me. It is largely rural and remote, and gets very little of the tourist traffic that its southern neighbour, the Algarve, gets.

For us, Alentejo contains many Portugal highlights which are scattered all around the region, and it made sense to devise a Portugal road trip itinerary in order to see them all.

Image of cork trees in Alentejo region on road trip Portugal
Cork trees are a common sight in the rural Alentejo region
Image of Monsaraz village at sunset.  A must stop on a Portugal Road trip Alentejo
Monsaraz village

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.

Portugal Road Trip Alentejo – Driving in Portugal

We have driven in several European countries, and found driving in Portugal very similar to driving in Italy. A little crazy but overall not too bad. Read up on the Portugal road rules before starting out and then be aware many locals will throw the rule book out the window and make up their own.

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. Even if you use satnav it’s a good idea to have a paper map as satnav can be hit and miss in remote and rural areas.

The most difficult part of driving around Portugal for us was getting around warrens of narrow medieval streets built 700 years before the advent of the motor vehicle. We got by without any dints and dents, but we had no space either side of the car in some places.

We also encountered the occasional driver quite happy to take unnecessary risks. Diving around to our left, overtaking us and then taking 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 is another who sticks in the mind.

Portugal Road Trip 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 Evora, where we stayed for three nights.

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, Portugal

Roadtrip Portugal Image of Evora Sé or Cathedral at night
Evora’s Sé, or Cathedral, is at its most magical at night
Image of the Roman Temple of Diana in Evora Portugal
The Roman Temple of Diana dominates this gorgeous square in Evora
Image of a house built into an arch in the Evora aqueduct
A house built into an arch of the historic Aqueduto da Prata
Image of the Igreja da Graça church tower in Evora
Evora’s Igreja da Graça church tower

Évora is 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 hotel, down an impossibly 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.

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 accommodation 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
Image of skulls and bones in the chapel
If only cremation was de rigueur in our day…
Image of the entrance to the Chapel of Bones in Evora
Our bones await your bones: the grim message above the entrance

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, but 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 Estremoz Saturday Market Portugal
Estremoz Saturday Market
Image of market stallholder at Estremoz Alentejo Portugal
A local character at the Saturday market in Estremoz
Image of antiques sign in Portuguese at Estremoz market
Art Nouveau style antiques sign at Estremoz Market

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.

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.

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 must be a stunning place to stay, 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 at sunrise
Marvao Castle at sunrise
Image of Traditional chimneys in Marvao Portugal
Traditional chimneys in Marvao
Image of Marvao Castle and formal gardens
Marvao Castle and formal gardens

Marvao, Portugal is one of most special places we’ve visited in Europe, a tiny whitewashed village straddling a narrow mountain-top ridge in the Serra de Sao Mamede mountains, with precipitous views down from either side, and Marvao Castle, the Castelo de Marvao, one of the most impressive of all Portuguese castles. This remote mountain fastness looks impregnable, and indeed was never captured.

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.

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.

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. It has one of the most beautiful settings of the many castles we have visited in Europe.

Image of Marvao village and mountains
Marvao village and mountains
Image of the main street in marvao village Portugal
Rua do Castelo, the main street in Marvao
Image of Marvao Castle Gardens Alentejo Portugal

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, Portugal

Image of Castelo de Vide street and Castle
Castelo de Vide street and Castle

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 Portugal 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.

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.

Image of Fonte de Vila Castelo de Vide Portugal
Castelo de Vide – Fonte de Vila

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 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.

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 Vicosa was somewhere we didn’t plan on passing, but we got a good view of the town’s famous marble quarries from the road, so here was another discovery to be revisited in the future.

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

Monsaraz, Portugal

Image of Monsaraz village at twilight
Monsaraz village at twilight

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

This whitewashed village and castle enjoys a beautiful 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 da Alqueva reservoir system to the east.

Image of Monsaraz Castle at dusk
Monsaraz Castle at dusk

From the walls of Monsaraz Castle, at the southern end of the village, you have a glorious view of Monsaraz 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.

Monsaraz Alentejo 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 the Monsaraz restaurants had closed, and we were left sharing the streets with a few cats.

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, just before dawn. If you’re looking for a hotel Monsaraz doesn’t have many options within the village, but if you search for Monsaraz hotels there are some options very close by in the surrounding countryside that are within easy reach.

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 Fonte de Telheiro fountain near Monsaraz Portugal
Fonte de Telheiro near 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 little flower-covered islands 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 Mertola town and Castle
Mertola town and Castle

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, and the start of our adventure there.

We’d heartily recommend a trip to the Alentejo – 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.

Image of David Angel found of Delve into Europe Travel Blog / Website

David Angel

David Angel is a British writer and photographer who has been travelling and photographing Europe for over 25 years.  His work is regularly featured in worldwide media including the BBC, the Guardian, the Times and the Sunday Times.

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