Driving from Lisbon to Madrid
 

We plan to drive from Lisbon to Madrid in December. I figure we should plan to stop for one night somewhere in or near Merida, Caceres or Trujillo, Spain. Does anyone have any suggestions regarding which city as well as specific places to stay?

Also, would love to stay in Toledo the night before our midday Madrid departure back to the states. Does this make any sense or is it too long a drive from Toledo to Madrid Airport (our flight leaves at 1pm).

Thanks for any advice you can send this way.