Heading southwest out of Madrid down to Merida to the Roman ruins, you’ll see Oropesa, a small town where nobles of Toledo stayed.
I, like most Americans, am a sucker for castles. We had one rule on this hastily planned trip. If we see an interesting castle or cathedral off in the distance, pull over and go check it out. We stuck to this rule for the entire trip, and was so worth it. So, we pulled over to get a look.
The castle was built around 1400 which you can climb to the top of for great views of the distant mountains.