1st Trip to Spain in October 2020 - Thinking Madrid and Extremadura

I don't think you'll be bored. I'm sure there are some other interesting places in the area, and with a car you'll be able to reach them if you have time. I was limited to public transportation. One place I liked that's not on your list is the walled town of Ciudad Rodrigo, which gets a few Portuguese tourists but seemingly no American visitors. It's west of the as-the-crow-flies route from Caceres to Salamanca. I don't know how much extra driving time that would be. Just west of C.R. is the attractive Portuguese town of Guarda.

Salamanca has a large historic district, plus the university, so it might require more time than you expect. On the other side of the coin, Merida has worthwhile sights (good archaeological museum) but is otherwise not an especially attractive place. It's not a place I'd choose to put an extra night.

You also have a lot of places often thought of as side-trips from Madrid that you could include if you feel you itinerary is a bit thin: Toledo, Segovia and Alcala de Henares. The latter is reasonably near the Madrid airport. I was seriously underwhelmed by Avila, but you might be driving right past it.

Hi! good on you for choosing Extremadura, an underappreciated and undertouristed region of Spain, steeped in history and culture. I think that October will be a fine time to travel there. As these are smaller towns and countryside, I agree a roadtrip is the best way to see this region.

Lucky for you Lonely Planet has a great article on Extremadura and places to see!: https://www.lonelyplanet.com/articles/unexplored-spain-roadtripping-around-extremadura

I would probably adapt their itinerary somewhat to include some things of your travel wishlist + plus my own picks:

Fly in to Madrid
Madrid (2 nights)
-Rent car and drive to visit Segovia & Avila
-Continue to
Salamanca (2 nights)
-Drive south and stop at Monasterio de Yuste (where HRE Charles V retired)
-Continue to Monfragüe National Park for the day
Cáceres‎ (2 nights) - day trip to Trujillo & Guadalupe Monastery
-Continue south to
Merida (2 nights)
-Drive south to
Zafra (2 nights) - Day trip to Jerez de los Caballeros
-Continue south to the town of Monesterio for the Museo del Jamón
-Finish driving to
Sevilla (3 nights) - drop off car here
-AVE High speed train back to Madrid
Madrid (1 night)
Fly out of Madrid

PS: October 12th is our National Day in Spain, so you will probably encounter closures of shops and restaurants in the small towns.

acraven- Ciudad Rodrigo looks beautiful. I think I need to map out my itinerary and figure out drive times. I think you are right about giving a bit more time to Salamanca.

Carlos- I've ordered the Lonely Planet Spain book since Rick's book was a bit light on the Extremadura region. I did see that article on their website. I really like your updated itinerary. I think that will work perfectly for me. On October 12th, would things in Madrid or Sevilla be open? I would probably try to time my trip so I was in one of the major cities on the holiday.

Thank you both for the suggestions.

Hello, glad I was able to help :)

Regarding the October 12th holiday, yes more things will be open in Sevilla and Madrid, certainly most restaurants and larger stores. Mérida, the capital of Extremadura may also have a good amount of options available. Most large tourist sites will still be open, but I would double check smaller ones like the Museo de Jamon in Monestario.

Public transport will run, but in Madrid, there is a huge military parade with the King of Spain, showing off some of the historic military units, that marches down the main thoroughfare of the centre of Madrid, this will have an effect on public transport and the busyness/traffic of the city. Sevilla may also have some events that I would double check when you get closer to Oct 2020.