Feedback on this Madrid and Andalusia itinerary?

Spain has tried to lessen the controversy surrounding the former Valley of the Fallen, now renamed Valle de Cuelgamuros, by having Franco’s body removed to another location. It is a somber location with the remains of thousands (both pro and anti Franco) interred there. As you are probably well aware it was built using convict and slave labor. When we visited we had a rental car,

If approaching the valley coming from Madrid on the AP-6 one can see the monument’s cross from about 12 miles away. From the cross one is afforded a nice view looking back towards Madrid.

The Valley is about 8 miles from San Lorenzo de el Escorial and an easy drive. How one gets there using public transportation I have no idea.

You might try Viator for a combination Valley of the Fallen and El Escorial tour:
https://www.viator.com/tours/Madrid/El-Escorial-Monastery-and-the-Valley-of-the-Fallen-from-Madrid/d566-2140JTEMA09
Or ask your local hotel or lodging provider directly for a recommendation. When I went I knew nothing about the Valley and a local resident of Madrid drove us to see it and El Escorial.

Also, you can erase from your post your explanation why you want to visit a place that is listed as tourist site in tourist guide books including by Rick Steves. They don't do politics here; moreover there are concentration camps that the Nazis under Hitler set up in Germany and Poland open as tourist sites today and no one ever questions that or explains why they are going to visit here on this forum
Other than that I think you might cut your rate of changing hotels so and do Cordoba as a day trip from Seville.

Sat, Oct 25 - Morning train from Cordoba to Madrid, then fly back to
JFK ~ 4 pm

This would make me nervous. Even if flight is at 4 pm you have to be at airport by 1 pm. We like to be IN our departure city night before a flight.

To avoid this you could travel onward on arrival (since you don't have big plans for Madrid that day) to Seville or Cordoba. Put all your Madrid nights at end of trip. We loved Cordoba and stayed 3 nights, liked it better than Granada.

Seville should get more time. 2 nights is only 1 full day for sightseeing.
Bus from Seville to Ronda is quicker, cheaper and easier. Then bus to Malaga as well, Buses in Spain are quite comfortable.
I would skip Gibraltar.

More time in Seville.

You're trying to see too much in my opinion.

I think within any trip, there's a point where transit, changing hotels, packing up, unpacking, repacking, finding a taxi to the train station, getting from the train station to your hotel takes up too much of the total vacation time. There's also a learning curve to some cities where learn more about how to be a temporary Madrileño on day 3 of visiting. If you put the time pressure of seeing everything in one day, I don't find it as enjoyable.

And, you're in your 30s, not your 80s. If you like Spain, and you will, you'll be back many times. You can save some stuff for your next few trips to Spain.

An example of what I would try is like: 4-5 nights in Madrid, 3.5 hour high speed train to Granada, 2 nights in Granada, 90 minute high speed train to Malaga, 3-4 nights in Malaga, 50 minute train to Cordoba, 1-2 nights in Cordoba, 1 hour high speed train to Sevilla, 3-4 nights in Sevilla, back to Madrid for your flight.

Hi everyone, thank you all so much for your helpful thoughts!

To the Artificial Intelligence comment — Thanks for the Viator link. Those are the kinds of tours we've been looking at for Valley of the Fallen, so I do think we'll end up choosing something like that. Fwiw, I only included the disclaimer about Valley of the Fallen after reading several other posts on here about it and seeing people warn about its association with fascism or advise against visiting.

We took took a lot of your advice (especially ChristineH, geovagriffith, Plectrude) and are thinking about cutting Gibraltar and Ronda to add some more time in Seville and Granada. Here's our new thinking:

Saturday, Oct 11 – Arrive in Madrid
Sunday, October 12 – El Escorial/Valley of the Fallen day trip
Monday, October 13 – Madrid
Tuesday, October 14 – Toledo day trip from Madrid
Wednesday, October 15 – Madrid -> Seville
Thursday, October 16 – Seville
Friday, October 17 – Seville
Saturday, October 18 – Seville -> Malaga
Sunday, October 19 – Malaga (Antequera day trip)
Monday, October 20 – Malaga
Tuesday, October 21 – Morning train/bus Malaga -> Granada
Wednesday, October 22 – Granada
Thursday, October 23 – Granada -> afternoon train/bus to Cordoba
Friday, October 24 – Cordoba -> afternoon train to Madrid
Saturday, October 25 - Fly home from Madrid

Abby,
Your revised itinerary looks better than your original.
My suggestion would be to go to Córdoba upon your arrival and leave Madrid to the end of your trip and thus avoiding one hotel change.
Consider this: Córdoba >> Granada >> Málaga >> Ronda >> Sevilla >> Madrid -with day trip to Toledo >> fly home.

Make sure to book your Alhambra tickets as soon as your itinerary is set.

Wishing you a wonderful trip!

I don't know anyone who thought that Gilbraltar was with the effort. I'd skip it and add a day to Seville.

Antequera is well worth a day trip but bear in mind there's no public transport to El Torcal.
Here's our day trip to Antequera
https://slowtravelitalyspain.blogspot.com/2020/01/malaga-in-november-day-8-antequera.html

Tinac - thanks for the link to your day there! That's what I thought on transit. We're planning to get a private guide for Antequera so they can also take us to El Torcal.

Priscilla - Thank you! We did consider moving Córdoba up as you suggest, but think we're going to stick with Madrid at the beginning for this one. We did just book our Alhambra tickets and reserved a guide mentioned in the Rick Steves book!

Many museums and other sites are closed on Mondays so make sure the places you want to visit in Madrid on October 13 are open. Same for Malaga on Monday October 20.