We rented a car in Lisbon for a road trip around the southern half of Portugal, and we have a confession: we had no idea where we were going, but it was going to be awesome.

As we drove straight east out of Lisbon without much of a plan except a guest house reservation in Évora, the south-central Alentejo region of Portugal stretched before us. This region is home to fields, farms, modest mountains, valleys, lovely people and a lot of history.

Sleepy Portalegre

Our first stop on our Portugal road trip was Portalegre, a town of nearly 25,000 residents, and not well-known for tourism. It was here, off the typical tourist route, that we found a white-washed town with narrow uphill streets of homes with yellow painted windows and laundry hanging outside. We sat down for lunch at Restaurante Cervejaria Santos for some coffee, olives and a light lunch.

Coffee at a cafe in Portalegre, Portugal

We explored the rest of the town center, finding pristine old streets and a large church where students were hanging out. As it turns out, many business close in this region of Portugal on Mondays, so there was not much to do.

White-washed buildings in Portalegre, Portugal Clothespins hanging laundry in Portalegre, Portugal Cobblestone streets leading to views in Portalegre, Portugal
Sunny streets with white and yellow homes in Portalegre Churches as a backdrop for a scene in Portalegre A quite street with no cars in Portalegre Post office azulejo art in Portalegre, Portugal

We drove on, but now a bit northward, to Castelo de Vide, a village Becca had read about and said we might as well stop by, as it’s not clear when we’ll be back.

Castelo de Vide, our favorite village

Castelo de Vide, a quiet town of 3400 people and only 17.5km from Portugal’s border with Spain, became our favorite Alentejo village. Because it’s harder to reach, Castelo de Vide is even farther off any tourist route. We took in the charm of the azulejos on the buildings, the steep hilly roads, the end of town from where we could see an expanse of farmland, and the historic synagogue and Jewish lane, which were once home to a tiny Jewish population. You can Explore More About the Jewish history of this village here. We couldn’t get enough of the scenery.

White-washed buildings in Castelo de Vide, Portugal Small white church in Castelo de Vide, Portugal
Art deco architecture in Castelo de Vide, Portugal Rusty gate outside a church in Castelo de Vide, Portugal Castelo de Vide, Portugal scene Holding up our Lonely Planet Portugal book in Castelo de Vide
Becca with an old street in Castelo de Vide Taking photos of the white homes in Castelo de Vide Hilly street that leads to a great view in Castelo de Vide
A hilly street with a biker in Castelo de Vide Tiny church building in Castelo de Vide A view of churches and buildings in Castelo de Vide View of white homes with red rooves in the hills of Castelo de Vide

The main event, Évora

Évora is one of the biggest attractions in the south of Portugal. Travelers go to Evora in substantial numbers to experience this medieval city. We arrived after dark to Hostel Namaste, which has nice outdoor space, friendly travelers and spacious private rooms that are like staying in an hold house. After having dinner at Mojo, a trendy burger place in a cellar, we found obligatory dessert at Uafas.

Sights in Évora

Évora is, to say the least, pretty touristy. In the morning we saw the market and Capela dos Ossos, the famous bone church, which was a bit overrated. We preferred walking around outside and seeing the grand plazas, stopping to sit down for coffee at Cafeteria 35, which is on a small street and feels like the set of a movie.

Rows of white homes and buildings in Evora

Becca and Dan on the roof of the Bone Chapel in Evora, Portugal

Town center and plaza of Evora, Portugal Taking a photo in a mirror on a quiet street in Evora, Portugal

Without much more to see in Évora, and we recommend one day here, we set off for the southern half of the Alentejo for what was in store for us there.