Help with Mapping Itinerary

I can only help with Toledo and Cordoba - 2 nights in each is sufficient. We spent 3 in each city because we’ve now moved on to a minimum of 3 night stays, if feasible, cause we move slower.

Well, it looks like your destinations are all over the place and you are backtracking a lot. I just went to Google maps and plugged everything in (I had to use the car option, not public transport, since there are multiple destinations) and wound up moving places around. For one thing Cáceres is more than 3 hours from Cordoba so a day trip would not really be feasible. FWIW, I love Cáceres - it was one of my favorite places in Spain.

At any rate , I moved the destinations around and this is what I came up with (it's a screenshot of the map I worked out). https://photos.app.goo.gl/yrSze7wBtNiuGFQw8

Obviously you can do this yourself and switch places around and add them to see what works and what doesn't. Google maps is a great tool to check distances and so on. You can also reverse the order, too.

We stayed a night or two in Segovia which I highly recommend and one night in Avila( our first night after landing in Madrid) which was not necessary. Perhaps you will have a long term rental in Madrid and ,thus, are visiting some of these important cities as day trips?

Valencia is an outlier and I’d leave it for a different trip. Two nights each in Toledo, Córdoba, Cuenca, Salamanca seems reasonable. Segovia and Alcalá de Henares would be good day trips.

Getting to the Valley of the Fallen (it does have a new name) from San Lorenzo Del Escorial would have to be by bus or taxi. It’s not on a train line and about 8 miles from El Escorial. We spent about two hours at the Valley.

If going to Salamanca, considering combining a short visit to Ávila with it. Ávila can be seen in a couple hours and not worth a separate day trip from Madrid.

In addition to Cáceres, consider visits to Trujillo, the Royal Monastery of Santa María de Guadalupe, and Mérida.

Since I always have a rental car, I can’t speak to the ease of using a train to get to any of the places. If you had a rental car, it would be easy to spend all 5 weeks in Extremadura.

For me it seems like your trip is zigzagging all over central Spain, east, west, north, south... making my head spin haha! To me trying to do this trip sequentially would be a major pain, especially without a car.

I think to keep your sanity you will need an unconventional solution. The center of all the zigzag'in seems to be Madrid, so my idea is to make that your long-term home base. Yes rent an apartment or airbnb in Madrid for 4-5 weeks, become an temporary Madrileño!

Then you can use Madrid as a springboard to make 2-3 night side trips to surrounding cities, like Salamanca, Cordoba, Cuenca, Toledo etc. Make sure to keep the Madrid apartment where most of your stuff will be, just travel light with what you need for each side trip. This makes the most sense because Madrid is the only city that connects all of these places by public transportation, like a spoke on a wheel.

When you are done fly out of Madrid, simplicity itself!

Thank you all for your thinking on this "zig-zagging" trip! What I am thinking now:
Skip Valencia for this trip
Use Madrid as hub and do maybe three loops out
Since we only travel light with one rollaboard suitcase, we can easily take our luggage with us
This is what I am now thinking:

Madrid (4 nights): a tour to San Lorenzo de El Escorial and Valley of the Fallen (too difficult to do on our own); Alcela de Henares

Salamanca (2 nights); not sure how to visit Avila with luggage, so probably will skip
Caceres (2 nights)
Merida (2 nights)
Seville (3 nights) - this makes sense because of train connections; we can take a vacation from our vacation here
Cordoba (2 nights)
Madrid (2-3nights) - day trip to Segovia
Cuenca (2 nights)
Train back to Madrid and straight to Toledo (2 nights)
Madrid - 3 nights; day trip to Aranjuez; fly out

Does this itinerary make sense? Is the number of nights in each place worthy? Any side trips I'm missing?
If we can rent a car in Caceres we could do a side trip to Trujillo. If so, I'd add another night to Caceres. Thoughts?

Thanks again for your help with this. I know I have some extra nights to "spend", but I could trim the number of days for this trip.

C

Madrid (4 nights): a tour to San Lorenzo de El Escorial and Valley of
the Fallen (too difficult to do on our own); Alcela de Henares
Salamanca (2 nights); not sure how to visit Avila with luggage, so
probably will skip
Caceres (2 nights)
Merida (2 nights)
Seville (3 > nights) - this makes sense because of train connections; we can take a
vacation from our vacation here
Cordoba (2 nights)
Madrid (2-3nights)
- day trip to Segovia
Cuenca (2 nights)
Train back to Madrid and straight to Toledo (2 nights)
Madrid - 3 nights; day trip to Aranjuez;
fly out Does this itinerary make sense? Is the number of nights in
each place worthy? Any side trips I'm missing? If we can rent a car in
Caceres we could do a side trip to Trujillo. If so, I'd add another
night to Caceres. Thoughts?

I don't think I would enjoy all the back and forth to Madrid, but then I did the somewhat loooong drive from Cuenca to Caceres, so I don't necessarily recommend that either. Merida is an easy day trip from Caceres. I think some further refinement is in order--I would put Madrid and the beginning and at the end, and maybe see if having a car for a little bit more than a day trip might make it smoother. We really liked having a car for the parks in Extremadura.

Glad to hear there is a bus to Trujillo. Much prefer doing that than renting a car. I am open to adding days to Salamanca, but what day trips would you suggest?

I am looking at eliminating the middle trip to Madrid. I guess I can just transit there and go to Cuenca from Cordoba. Does that sound like it would work?

Thanks for all the good suggestions all. I truly appreciate your thinking about this.
C

A change in Madrid will be required, but the trip from Cordoba to Cuenca can be made in less than 4-1/2 hours at various times of the day, though some departures take longer. I'd want to stick with a single carrier, not a combination of Renfe and Iryo; you'll see offerings with that combination (as well as some mixing bus and train) if you search on thetrainline.com rather than renfe.com.

Thanks everyone for your help. I am slowing this journey down and adding suggested day trips when bus connections are available. Most places we will be staying for 3 days.

Somehow when I first started planning this, I neglected to factor in Easter Sunday. Is there any place on the itinerary I should absolutely avoid for Easter, or is there a place I should absolutely be for Easter. I am figuring wherever I am, the lodging prices will be pretty inflated.

Thanks again,
C

From personal experience I can tell you that hotel rates go up a lot in Seville for Holy Week (the entire week). I paid more than double the typical April rate in 2019. I also had to agree to a 2-week cancellation period, beyond which I would be charged for the entire stay (which I think was 6 nights).

Not all cities experience that extreme an uptick in rates, even within Andalucia, which is perhaps the area most affected. I'd suggest pricing out places of the caliber you prefer on booking.com for Holy Week so you can try to avoid being in the most expensive cities during that period.

Caceres is absolutely worth a night. The tour busses leave and the city is glorious. Since you’re foodies, the area around there is ridiculously awesome for pork and the local cheese. Beautiful day trip opportunities to small villages and national parks if you decide to rent a car for just that part of your trip. ( that’s what we did)

Cordoba was one of my favorite cities in Spain. I’d spend an extra day there given your long trip.