Need help with itinerary: 20 day trip

I have driven all around Spain (and Portugal, and France, and Great Britain, and etc., etc.), but the questions I always ask myself when I create itineraries are why do I want to go to a certain place, what do I specifically wish to see or do, what is a feasible amount of driving time each day, do I allow sufficient time for sightseeing, where do I want to stay (not just cities, but also specific hotels), and is there an element of flexibility for me in my travels.

One thing I really dislike is having to pack and unpack and check in and out of new hotels day after day. I also worry a bit about touring while my luggage is in the car that is parked somewhere. Therefore, I try to create itineraries that allow me to stay in one hotel for two to three nights minimum with my luggage safe in the hotel. What is a reasonable amount of time in each place? When I meet the goal or accomplish what I have highlighted for visiting in that area on this particular trip. I never think that this will be the one time in my life I will be somewhere so I have to see everything all at once.

Yes, your itinerary is somewhat feasible, but is it enjoyable? First, you will have jet lag when you arrive, and you will be quite tired. I am guessing you have to connect through Madrid to get down to Malaga. You will arrive at Granada in the dark--will you really have time to see the Alhambra and other sites in a relaxed manner the next day before you jump back in the car and drive to the next place?

Do you really want to zig zag up and down through the country just to check cities off your list? Your question about Valencia concerns me--I do not think you have done enough research about each place you say you want to visit in Spain.

What kind of "day trips" do you want to take from Madrid? The most popular one is a visit to Toledo! How will you get to the countryside in the Basque region without a car?

I would try to reduce the geographic coverage of your trip and try to focus a bit more on rich, meaningful experiences. You could spend a week just in the South of Spain, a week just in Madrid and surrounding areas, or a week in the northeast of the country. You would still miss out on many great places! You have to prioritize what matters most. I think you need to learn a bit more about what each place offers before you finalize this trip. Best wishes.

I would definitely not try to add another stop to this itinerary. It already feels aggressive to me. If you had more time, I'd be suggesting you add Malaga rather than Valencia; it would work better logistically.

I agree that one day--possibly still rather jet lagged--is really short for Granada. The Alhambra is a large complex that can take close to a full day to see. When will you have time to see the city's other sights? The Alhambra sells out early. Have you checked to be sure tickets are available on the day you'll need them?

Via Michelin estimates the driving time from Granada to Ronda/Arcos/Sevilla at 5 hr. 14 min., and that's with no stops or traffic delays. Ronda isn't a little village you can see in an hour (for that matter, Arcos is large enough to need more time than that). In both those places you'll have to park the car, then walk from the parking place to whatever you want to see. That's going to be a long day in the car, some of it on curvy roads where you might be held up by other vehicles. You could well need more time than ViaMichelin estimates for the driving. You'll need at least one meal sometime during the day, which will extend the travel time. It will be quite late when you reach Seville, and you're going to have to deal with parking the car. Then you're in Seville for just two days, which I think is a day short for Seville.

ViaMichelin estimates 4 hr. 40 min. for the drive from Seville to Salamanca--again a best-case figure without any allowance for stopping, traffic, a search for parking or eating. Salamanca has a large historic center; you won't have time to see much of it, and on the way from Seville you will have blasted past both Merida (Roman ruins) and Caceres with its UNESCO-listed Renaissance core.

Then the next day you're back in the car again for a significant drive to Madrid, maybe by way of Toledo. I really discourage that. In addition to the drive itself (over 4 hours), you'll lose time parking the car and getting from the parking place up to the medieval center of the city. Toledo has a lot to see and you'll only have about half a day there. If you want to see something on the way to Madrid, I'd recommend Segovia instead. It will mean nearly an hour less in the car, and--though it does have more than a few hours' worth of sights, it's not as sight-rich as Toledo. El Escorial would take you even less out of your way, but I haven't been there so I can't comment on how its sights stack up against Toledo's and Segovia's (in both of which cities I spent multiple nights).

I don't see time for the Basque countryside in the schedule. You have little more than a day to see the two cities. I don't know where you'd fit in a nice country walk in the south, either.

I like all the places you want to go and don't blame you for wanting to see them, but I'm afraid this is going to be a tiring trip except for the time in Madrid and Barcelona--and the need for prebooked, timed tickets at so many sights in Barcelona somewhat limits the typical visitor's ability to relax and play things by ear.

I'd drop Salamanca and maybe the Basque Country. Your transportation time would be reduced a lot if you traveled from Seville to Cordoba (spending one night there rather making a round trip on the train), then straight to Madrid. Both Toledo and Segovia work as day trips from Madrid. Spain has super-fast trains running from Seville to Cordoba to Madrid to Barcelona, and you're not taking advantage of any of them.

Sevilla to Salamanca is a 4.5 hours drive while Salamanca to Madrid’s airport is about 3 hours (direct). Add a couple hours if going to Toledo.

It would be a shame to drive to Salamanca and not stop en route somewhere, whether it be the places acraven mentioned or other equally interesting towns.

I’d choose Toledo over San Lorenzo de El Escorial (El Escorial is a short distance away.) any day of the week. The Royal Monastery is the main draw in San Lorenzo de El Escorial. Between Salamanca and Madrid you could stop in Toledo.

There are some free parking lots on the Roman Circus side of the town, e.g., Aparcamiento de Santa Teresa, and around town. Bookmark them on your navigation system so you can go straight to one of them. If you wanted a pay lot, when entering the historic center via the Bisagra gate continue straight on that street. You’ll pass Plaza Zocodover on the right, then the Alzázar on the left. At the end the street turns left and there are a couple parking garages. Personally, I’d avoid driving in the historic center.

I would definitely not drive to Granada upon arrival in Malaga. In fact I wouldn’t rent car at all. You only need it arguably for Ronda and Arcos. If you really don’t want to stay in Malaga (and if not, I’m not sure why you’re flying in the first place), take a train to Granada from Malaga, train or bus to Cordoba (spend a night there) and train to Sevilla. You really just don’t have the time otherwise for all that you’ve listed for Andalucia.

I would also delete Salamanca from the trip. Add that night to any of your other stops.

Spain is a wonderful place to just absorb at a slower pace. I think you’ll have more fun if you park your itinerary.

Sorry, I don't see any point where you would have time for even a short hike.
I would not drive two hours after an overnight flight arriving at 5pm. Will both of you be on the contract and able to drive? (I am assuming it's a couple traveling since you said "we".)
Driving short distances in Spain to take advantage of rural areas is fantastic--driving long distances served by train is grueling.
An easy adjustment would be to eliminate the Basque region and add those days to Andalucia. I would also do the Salamanca and Toledo day trips from Madrid. That gives you longer stays in fewer places but far more enjoyment.
Then you would have time for some of the stunning outdoor areas in Andalucia--great hikes near Ronda. You can set off right out of the town, or take a bus/train to a good hike at Montejaque. Or if you have a car, drive to Grazalema.
I would drop the car in Andalucia and take a train to Madrid, train to BCN.

Thanks to everyone for the helpful information and critiques. My revised itinerary is below. I welcome all suggestions and thoughts, though my arrival and departure flights are fixed--dictated by prices, routes, and availability. Yes, I do prefer to travel faster than most people, and am a seasoned traveler, used to traveling in Europe as well as in other parts of the world. As to what constitutes “rich and meaningful experiences,” de gustibus non disputandum est.

1: arrive in Malaga 5 pm; rent car
2: drive to Ronda
3: Ronda & other towns / walks; stay in Ronda
4: hill towns / walks; drive in pm to Seville, return car
5: Seville
6: Seville; late train or bus to Granada
7: Granada
8. to Cordoba and then onto Madrid via train
9. Madrid
10: Madrid
11: Madrid / Toledo
12: Madrid / El Escorial
13: Train or car to Salamanca
14: Salamanca / get car / drive to Basque Country
14: Basque Country
16: Basque Country
17: Basque / return car / flight to Barcelona
17-19: Barcelona
20: Depart AM

A few notes:
Our route around Andulasia is not the fastest travel time, but I want to put Granada last, both for ticket availability and so that I am largely adjusted to the time change when I see it

That is much improved! I would still save Basque country, but you have to choose what calls you.
All will say more time in Sevilla, but you have to make the calls. (You could possibly cut a day from Madrid.) enjoy!

I personally think you’re still covering too much and you’re underestimating how much time it takes to move from one location to the next and to get your bearings.