How We Explored the Alentejo Countryside

Portugal's Alentejo region is simply stunning! Amongst its cork and olive plantations, there are well-known wine routes, quaint medieval towns and hidden megalithic complexes.

If you are interested in exploring the countryside of Portugal, this is a must region to visit - just rent a car and go on driving.

After departing the historical town of Évora, we took a day to explore the area’s countryside. We drove across the Alentejo until the village of Monsaraz, stopped along the way for some wine tasting and visited a prehistoric site as we headed to our final stop: The town of Óbidos.

Some Pêra Manca Wine on the Way to the Castle Town

Cartuxa Winery was our first stop outside the walls of Évora. The winery makes the region’s most famous wine, the Pêra Manca, and offers a shop for visitors to buy its wines and olive oils.

Cartuxa was the first of many wineries we passed by as we drove through the region. The Alentejo is widely known to be one of Portugal’s biggest wine areas housing a mix of small and large wineries.

From Cartuxa, we headed east towards the walled village of Monsaraz. The drive took less than an hour and it was so stunning that it made up for our whole day’s trip!

We passed by fields upon fields of yellow grassland, dotted with olive and cork trees. It was mid-September and the grass was so yellow that it played a beautiful contrast with the trees and wine fields that run along the highway.

Castelo de Monsaraz is perched atop a high mountain and you can start seeing its village’s iconic white buildings as you approach from below. Exploring the town was a highlight of my day especially because Monsaraz truly looks like it has stopped in time.

Its 16th century whitewashed homes take over most of the town and its narrow cobblestone streets lead to downhill alleys where the whole region can be seen from above. The village has several local restaurants and shops which were convenient for a quick bite before we got back on the road.

Some Esporão Wine on the Way to Óbidos

As we left Monsaraz on our way to the walled town of Óbidos, we stopped at one of the most famous wineries in the region: Herdade do Esporão.

I had never heard of Esporão before our visit but later discovered it is a renowned wine brand around the world. Once we got back to Boston, we actually started noticing Esporão wines being sold in several stores - I guess I had never paid attention before.

Esporão is located only twenty minutes from Castelo de Monsaraz, but our drive there took a little longer than we were expecting as the roads leading to the winery constantly weaved through vast grapevine fields.

Tip: Since we were running short on time, we stopped at Esporão’s store for some quick wine tasting. However, the estate offers additional attractions for its visitors such as a large restaurant and tours.

Our Final Stop: The Megalithic Complex

During my research for this trip, I discovered that Portugal has megalithic complexes scattered throughout the country and the Alentejo region has a great number of them.

Only forty minutes west of Evora, through dirt roads and cork tree plantations, we arrived at the Cromlech of Almendres. This large megalithic complex contains both menhir stones and cromlechs that date back between 5000 and 4000 BC.

The complex’s large stones are placed close to each other on an open field that overlooks a sprawling countryside.

Since it was already getting late, we had the area all to ourselves and with the stillness of the place - standing in what it seemed the middle of nowhere - I could only think to myself: Why was this specific spot chosen to have a monument? What was so special about it?

From complex, it was an easy two hour drive west to the Medieval Óbidos.


The Wrap-Up: We left Évora in the early hours and drove east across the countryside until we reached Monsaraz. After exploring the medieval town, we drove west passed Évora, and reached Óbidos at around 8pm. A great aspect of this drive is not only Alentejo’s stunning landscape but also the several small and large wineries that dot the area.

The B&B: Casa de Campo São Rafael is a quaint hotel located in Óbidos, near its historical center. We decided to stay at a hotel outside of the walled town so we could park our car with more ease. If you are driving, I would recommend that you do the same, because once you enter the historical town and see its narrow, pedestrian- filled streets, you will be glad you did not park inside it!

- Want to see the full trip and plan your next? Check out our Portugal Two Week Itinerary!