Short trip to Spain- looking for advice.

Caceres is a very interesting, non-touristy place. Also in that area are Trujillo and Merida. Merida is primarily of interest for its Roman ruins and archaeological museum.

You don't mention having been to Toledo, which I really love. Although it's close to Madrid, it's worth spending 2 or even 3 nights there so you can really enjoy it.

I suggest picking up a guide book with comprehensive coverage of Spain. The Rough Guide was published in March 2018. The Lonely Planet book is more up to date (November 2018).

Here are some potential small towns and cities in the Extremadura region of western Spain, in between Madrid and Sevilla, some of which Acraven has already touched on:

Cáceres: The old town of Cáceres is a UNESCO World Heritage Site and has a mix of Roman, Islamic, Gothic, and Renaissance styles.

Trujillo: This town is where some of Spain’s most famous(infamous) conquistadors came from. The town has a few baroque and Renaissance palaces and an interesting Museum of Francisco Pizarro, who led the expedition that conquered the Inca Empire.

Guadalupe: Has the beautiful Real Monasterio de Guadalupe. You can tour this monastery and its collection of art, jewels, illuminated manuscripts. You can also see two cloisters, one late-14th-century Mudéjar, the other Gothic.

Mérida: Has the best Roman ruins in Spain, designated a UNESCO World Heritage Site, the ruins are found dotted throughout the modern city of Mérida.

Badajoz: Capital of the Moorish kingdom, the Taifa of Badajoz. It has a nice Moorish historic quarter. The town is dominated by the Alcazaba, a 9th century fortified Moorish citadel.

Zafra: A white-washed walled town nicknamed "Little Sevilla", feels very Moorish. They filmed some scenes from the T.V. show Game of Thrones at the nearby Castillo de Feria, an Moorish hilltop fort.

Jerez de los Caballeros: A very picturesque small town. The old town is surrounded by a Moorish wall with six gates. After it was conquered from the Moors, the town was transferred to the Knights Templar, who left their own architectural mark.

Any one of these towns are worth a couple of nights, hope this gives you a few ideas :)

The above suggestions are the "westerly" route roughly following the A5/E90 and E803 and would be very fine - I'd also consider brief stops in Galisteo or Plasencia, if time allows. I wasn't greatly impressed by Merida, but then I've seen a lot of other, better Roman ruins over the years, including in Rome! We've driven roughly this route and as well as the towns, there's some interesting, in a bleakly beautiful sense, countryside to drive through.

A slightly longer alternative is an "easterly" route, roughly following the A4/E5. This takes you through proper "Spanish Spain" of Castilla-La Mancha. There are also plenty of stops worth visiting such as Toledo, Consuegra (windmills!), Almagro, etc. Then, over the border in Andalucia, are Ubeda & Baeza which are both stunning. Several national parks to visit too.

Since you have to go back to Madrid, perhaps you could do both routes, one south, the other north.

I'd also recommend looking into the paradores website for places to stay on route. Some are very good value, especially out of high season.

P.S. I'm doing the above from memory, so do double-check my motorway numbers. Spain has an insanely bizarre road naming system and I may well be wrong with the ones I've given.

I liked Cuenca a lot; for me the combination of picturesque town and two modern-art museums is hard to beat. But Cuenca is basically east of Madrid and about a 2-hour drive each way. It's much faster by AVE train, but the train drops you at a station about 3 miles from the center of town, and I don't know how frequent or reliable the bus service is. I remember noticing that it ran less often on weekends (and possibly not at all on Sundays?).

Thank you for the great suggestions. We’ll do more research on the places you suggested. Getting excited about our trip.

I really enjoyed Toledo, but I wouldn't want to drive there. It's much easier to visit by train (spur line) from Madrid, either as a day trip, or even better as an overnight. If you have a lot of luggage, store it at Atocha station, take a small overnight bag to Toledo, and then pick up your luggage and rental car when you return to Madrid. BTW a friend just got back from Merida and raved about it.