I can agree with John on his list, was in Toledo, Segovia and Trujillo last
September and they are all wonderful. Toledo is packed with tourists but the
cathedral and the town itself are wonderful to just walk about and John is
right in the evening there's nobody around!
Trujillo is a quiet town, and its nice to explore on foot, walking up to the
castle and admiring the views from the top of the hill. And the plaza is
great in the evenings in summer! Segovia is great, especially if you can get
a room at the hotel infanta Isabel with a view of the plaza!
We also went to Caceres, which is a bit west from Trujillo, very nice old
town as well, beautiful buildings in the old part. ON the highway from
Plasencia to Caceres you can also take a detour to see Garrovillas, which is
a cute typical Spanish village with a beautiful arcaded plaza mayor and all
the arcades and buildings are askew!!
We also stopped for a couple of nights in Jarandilla la Vera, a nice quiet
village in the Sierra de Gredos (if I remember correctly), great for some
relaxation in the parador (and excellent food), beautiful scenery around in
the mountain passes...
Another place we stopped at was guadalupe - in September they have the
village feast which is quite nice to see, also great for the scenery.
Last place we visited was Oropesa, nothing special about the village, except
for the castle which is part of the parador (which has an excellent
restaurant!) but we used it as a base to see some other places like
lagartera for buying some lace and talavera de la reina (an industrial town,
but well known for the ceramics they produce)
When I have some time I should write a detailed report, but feel free to ask
directly on the places we visited. I would suggest getting the Michelin
green guide, it helps a lot with choosing which places to see...
Cheers
gianfranco