This is what I'm considering...
Fly into Madrid, take a train to Toledo for 2 nights. Pick up a rental car, head to Segovia 2 nights. Salamanca, via Avila, 1 night. Then into Portugal...
Here is where the specifics break down a bit, but Douro Valley and Porto seem worth 2 nights. Coimbra at least for the day. Between there and Lisbon is a region known for roasted suckling pig that must be sampled and lingered over for a full night.
Lisbon 3 nights, still in the rental car. What can be done to make this as painless as possible? Is there a convenient train station lot in the suburbs where the car can have its own vacation for the duration? Maybe a good hotel recommendation that's not too hard to drive to, with an affordable parking garage?
Then we'd give ourselves two or so days (overnight suggestions welcome) to make it to the white hill towns of which Rick writes so fondly. Finally to Granada to drop the car off.
Taking the train back to Madrid, via Sevilla and Cordoba a few nights each, should a cinch for the final, longish week of this whirlwind excursion.
This is scheduled for the last half of October, into the first half of November. Who wants to talk me out of this?
At first I thought to take the train into Portugal, pick up and drop off a car on either side of the Lisbon stay, but the only train out of Salamanca leaves at 4:30 in the morning and takes four hours to get to Coimbra. Not to mention no train service at all from Portugal to Spain's hill towns. Is there a bus option I haven't considered? Thanks for any help!