Driving from Lisbon to Madrid
 

I will be spending a week or so in the Lisbon area this July, and will then need to deliver a car back to Madrid. My companions and I will actually have several days to get from Lisbon to Madrid. (At least 3 days, possibly up to 6). The drive itself could easily be accomplished in half a day, but we would love to make a true roadtrip out of this. I would love recommendations for any stops/side-trips we could make in the region. We are two young couples who love food, drink, and history. Thank you!

Cáceres, Mérida,( amazing archeology museum and Roman amphitheater, Trujillo, Guadalupe.. Oropesa ( beautiful castle )..just to name a few.

See where the explorers who went to the Americas were from.. very very cool historic area of Spain.

Don't just skip over Portugal like the first comment did ! On the motorway from Lisbon do stop off in Evora - a beautiful medieval walled city - and maybe do a short detour further on to Monsaraz or Marvao, both tiny hilltop villages that time forgot.
I second the idea of Caceres, though, a lovely place.

If you are near Salamanca do stop there..possibly the most beautiful plaza major in Spain, wonderful university buildings, thankfully very little if any graffiti, on the roman road/ la plata and reasonably priced as it is has university geared prices and is a true delight.

I'm not familiar with the Portuguese side of the route. Glad you added some other places. Now if only the OP would return!

Thank you for your comments! Sorry for the radio silence:)

Our travel plans have actually changed a bit. We will still be heading to Spain from Lisbon/Cascais, but will now be stopping in Seville and Granada before Madrid. I've spent time in these towns in the past, but recommendations are always welcome.

Thanks again.