Southern Spain 21 days Itinerary thoughts?

We spent 11 nights in that area in Sep 2023. (With so little time we dropped our original plan to spend 1 night in Toledo and instead added Cordoba based on advice from a forum member; it worked well for us as the Mezquita was a unique site.):

• SEVILLE 3 nights
• RONDA (with visit to Setenil de las Bodegas) 2 nights
• GRANADA (with visit to Montefrio) 2 nights
• CORDOBA 1 night
• MADRID 3 nights

Our trip report might be useful reference: https://community.ricksteves.com/travel-forum/trip-reports/trip-report-spain-aug-sep-seville-ronda-granada-cordoba-madrid

Thanks for your excellent report.
I will be studying it to help plan our trip!

First off, thank you for describing your interests and priorities. It makes it so much easier to offer suggestions.

I think your itinerary is good. I can't comment on the bus vs train vs rental car questions. My preference is always for public transportation over driving a rental car, and I'd rather hire a driver to take me to places than rent a car for places hard to reach by bus or train.

If your flight arrives in Madrid early, and you can get to Toledo late morning, and you aren't zonkered, I think you can enjoy the highlights of Toledo in a day and a half. Two full days would be better, and if you need some downtime on that first day, then adding a third night in Toledo probably makes sense. Whether to take it by skipping Ronda altogether, or by subtracting a night from somewhere else is hard to say. Ronda is lovely and very different from everywhere else on your list, but if your consideration is to eliminate a lot of moving around, that might be a place to cut.

How many nights are you thinking for Extremadura? The only place in Extremadura I've been to is Mérida, which is probably worth a half-day if you're nearby, but I'm curious what draws you to that region?

Good question. We enjoy some time in the out-of-the-way places that still have history and ambience.

So we're thinking Extramadura would offer stays in paradors (there's one in Caceres and one in Trujillo--both are medieval walled cities), some Roman ruins, small museums, and just some time away from big cities and mega amounts of tourists.

Perhaps someplace else would fit the bill, and still be within our time limitations?

Also, I think Ronda is now added to a really-want-to-see list.

We visited mostly Extremadura on our 2024 trip. On it we stayed at Paradors in Mérida, Cáceres, Plasencia, Trujillo, and Guadalupe. We stayed at others too that were not in Extremadura.

My trip report for that trip: https://community.ricksteves.com/travel-forum/trip-reports/spain-mostly-extremadura

Photos from that trip are at: http://jaimeelsabio.com/vac_pages/2024vac1.html

Mérida - Paid parking at the Parador, in its garage.
Plasencia - The Parador has its own garage, but we found free street parking a couple minutes walk away.
Trujillo - free parking beside the Parador or very close by.
Guadalupe - Free street parking a couple minutes walk from the Parador.
Cáceres - The Parador is in a vehicle restricted zone. It recommended a pay parking garage about a mile from it. We found a large free lot near that parking garage. Taxi from the Parador to the parking lot was €6.

I'd skip Ronda. Arrive Madrid and take the train to Cordoba (3 nights; or 4 if you visit Medina Azahara just outside Cordoba). Then train to Granada (2 nights) and Seville (4 nights), Use a rental car to visit Merida (2 nights), Caceres (1 night), Then drive to Toledo (2-3 nights) stopping at Trujillo on the way. If possible, drop off the car in Toledo. Train to Madrid. If a 21 day itinerary includes 2 days for arrival and departure, this leaves you more than enough time for Madrid.

I am a bit concerned about the travel in November from Merida through Trujillo. I've enjoyed that area, but never in that time of year and I'd be a bit concerned about weather conditions. Maybe others can provide more information.

Responding to Anita’s comment, I doubt the weather would be bad in most of Extremadura in early November. If you were headed into the Sierra de Gredos mountains, then yes, it could be cool/cold at night.

Thank you everyone!
jamieelsabio, I appreciate the input on the paradors!
Anita, thank you for proposing an alternative itinerary. We will be considering this!
As for the weather, fortunately we have lots of latitude planning so far ahead. I will look at weather in both October and early November at temperatures and rain. That may help us decide.

I see the point of going straight to Toledo. The only downside is jetlag, but you know best how you handle it.

If you are concerned about weather in Extramaduro, maybe get a car right after Toledo and do that first ( I haven't been to that area yet). Then continue to Ronda and other hill towns. Arcos is worth a half day and Ronda is a good base for 2-3 nights. Then drive to Granada and drop the car. Then drop the car in Granada, train to Sevilla, train to Cordoba, train to Madrid.