Abandoned castles in ruins, citadel castles on mountaintops, city center castles turned into hotels: you can find a whole range of glorious historic buildings in the Alentejo region of Portugal. You may think you need to travel to more northern parts of Europe to find castles within biking distance of each other, but in this sunny part of the south there’s a whole wealth of them.
You can indeed take a leisurely, self-guided bike tour of Alentejo like I did, or you can get around more quickly in a rental car from Lisbon. Either way, you’ll want to take your time exploring as this is an area where nothing seems to move very quickly. It probably never did unless there was a war going on. These days when you visit the villages or ride on roads between vineyards you seldom see another car. Bikes, tractors, and donkeys seems to fit the pace better.
Here are a few images from this region of olives, cork trees, sheep cheese, and wine.
Estremoz is a sizable town at the bottom, but the original village is on a high hill behind a real moat and wall: you actually have to go across a drawbridge to get to this castle. But then you can spend the night there if you want, passing by armor, tapestries, and weapons from the early 1300s when the part pictured above was completed. It’s beautiful and evocative Hotel Rainha Santa Isabel, one of many upscale inns with character that are part of the Pousadas of Portugal group.
The 15th century one below in Alvito is part of that group as well, a lovely inn dominating the center of this countryside town of 2,500. The main other draws are a hodgepodge main church that’s like a mongrel dog, and the much more harmonious Ermida de Sao Sebastião from the 16th century. I found a guy with a key to open it up and then a woman came and gave me a guided tour in Portuguese, explaining all the frescoes in detail. I sheepishly gave her a couple euros as a tip—one for each word I understood apart from “Christo.”
Some of the most interesting castles of Alentejo, however, are the ones where you have to use your imagination and go back in time. Some have been abandoned for centuries while the world has moved on around them. In the case of Terena, the castle is part of a town that was probably once a thriving place, but now it’s as sleepy as most of its neighbors. You can still tour it and walk around the walls, but when I was there in may the center behind the fortifications was mostly a wildflower collection.
The Castle of Valongo, on the other hand, has nothing around it but vineyards. It’s a rather ghostly, mysterious place, all locked up and closed by the landowner who is apparently more interested in growing wine grapes. You can go up and walk around it, but that’s as far as it goes.
I think the place I’d most like to go back to, however, is Monsaraz. Maybe I was so relieved to be walking around the cobbled streets after the hard-core cycling climb after a day of already riding 30 miles, but it felt magical. This is a place that could be the setting for a whole European history lesson. Captured from the Moors in 1167, it was then run by the Templars, while fending off attacks from the Spanish. Then the Earl of Cambridge trashed the placed after a marriage proposal got snubbed. In the late 1300s, Don Juan of Austria seized it in a surprise attack by teaming up with Spanish forces. This all happened before the year 1400…
You can spend the night within the walls of the mountaintop village in one of the historic B&Bs, or go more upscale and roll down the hill to Horta da Moura, with a well-known restaurant, a lounge with a billiard table, and a grand swimming pool. If you want to explore the area while basing yourself in a larger city, Evora is the best bet.