A driving loop through Spain and Portugal

Can’t you add a few nights in Madrid? It seems such a shame to miss it. We have been there several times and prefer it to Barcelona.
Otherwise, I like your stops. We especially loved Galicia, Santiago de Compostela is a must see. We stayed at the Pousada on the main square and watched the Pilgrims as they arrived. This Pousada was built by Isabel and Ferdinand as a hospital for the pilgrims.
Our first stop in Spain after leaving Portugal was in Baiona in a waterfront Parador. Loved it there. One of Columbus’ ships returned to Baiona from the New World , without Columbus as we learned in school.
This is near Pontevedra. That whole area is wonderful. Look at O Grove in the Rias Baixas too. Stay in Paradors whenever you can. The govt turned historic buildings into hotels and we have loved all but one of them on several different trips to Spain. Portugal has a similar program, Pousadas, and they are wonderful too. They all have restaurants serving the region’s foods.

Are you flying from North America to Madrid? If so, don’t expect to sleep on the way over. Instead take a direct (no transfers) bus from Madrid’s Barajas Airport to Toledo and spend the night. The next day rent a car in Toledo outside the town center.

Unfortunately, there's a good bit of very dull countryside around Madrid. I don't know how far it extends in the directions you'll be going or returning from at the end of the trip.

If you only spend your arrival night in Toledo, you really won't have time to see much of the city. Won't you be somewhat sleep-deprived and jetlagged after the overnight flight? Toledo is one of my favorite places, but the historic upper town has some hilly areas. Its medieval center isn't vehicle friendly, so I'm not sure how well this destination will work for your husband. Perhaps the little tourist "train" will be adequate for you.

Granada has some hills; the Alhambra is distinctly uphill from the center of town. I don't remember what the terrain was like between the entrance and the Nasrid Palaces.

Lisbon is also very hilly.

The area around Pontevedra (Galicia) has some of Spain's prettiest scenery, so that seems like a good area to spend a few days.

If you use ViaMichelin.com to plot driving routes and zoom way in, the most scenic roads will be outlined in green.

Thanks for these thought!
We have never been to Portugal, but we been to Spain several times before, just not to the south - so we've spent time in Madrid, Barcelona, Santiago de Compostela, Bilbao, Asturias, and Rias Baixas. This is a loop of places we still want to see. I'm sure it won't be our last trip to Spain. My husband was born in Galicia and we love all of Spain. We plan to get and return the car at the airport to avoid the drop off fee and we have a nice place to land (and nap) outside of Toledo after just 1 hr of driving. We'll probably do something like take that "train" and then do a little walking in town. I know we can't both get up the hill, but maybe he will find a nice cafe and I can do some climbing and viewing for an hour or two -- that's how we roll.

There are exterior escalators in Toledo that will assist you in the climb; I don't remember whether they take you all the way to the top. In any case, you'd probably have a walk to get to the base of the first escalator. There is bus service from the train station and the bus station; I don't know what the other stops are. The little tourist train almost certainly stops at both the train and bus station. I hope you can figure out a way for your husband to ride it unless you opt for a taxi.

Hi!
Your planned route is relatively fast-paced, but not too much so, in my opinion.
Are the flights booked? If not, it would make sense to fly to and from Lisbon (direct from Boston on TAP & possibly other airlines), because it would reduce the length of car rental: you do not need a car at all in Lisbon and Porto. So, you could start with 3 nights in Lisbon, take the train to Porto, rent a car in Porto for the rest of your trip as planned, with maybe 2 nights in Salamanca between Pontevedra and Toledo (skipping Madrid altogether since you do not plan to visit), and spending a final night in Lisbon again right before your flight. As a bonus, the flight would be a bit shorter and the time difference would be 1 hr smaller.

But if the flights are booked already, no big deal.
A good stop for 1 night between Pontevedra and Madrid would be Zamora, or Salamanca.
The 1 night in Toledo at the beginning will not leave you with much time to visit Toledo itself, but a few hours there can already give a pretty good overview.

As balso suggested, both Salamanca and Zamora are nice stops. Closer to the mid-point between Pontevedra and Madrid is Puebla de Sanabria. Closer towards Madrid are Segovia and nearby Real Sitio de San Ildefonso. For a night closer to the airport consider Alcalá de Henares, 25 minutes from the airport. Another possibility is Manzanares el Real. It’s 35 minutes from the airport.

I couldn’t even begin to suggest all the wonderful places you’ll be bypassing to get to the places you intend on visiting. There are simply too many.

The escalator just west of the Bisagra gate in Toledo (Escalera mecánica del Parque Recaredo) will take you all the way up to the historic center.

More time needed in Douro River Valley. Take the train up to Regua and enjoy.

Wow, so many great comments! Thank you all. The escalators in Toledo should be a big help and I appreciate the ideas on places to stop over enroute back to Madrid. Via Michelin will be a good resource with scenic routes, thanks for that, acraven. Our tickets are already purchased, balso, otherwise flying into Lisbon could have been a good move. I know that we will be missing lots of things this trip, but again, we will be glad to visit and see the places we do get to and I'm still open to hearing suggestions along out way!