If it is castles you are chasing, I recommend at least two towns just south of Badajoz and Mérida. Olivenza has two or three architectural points of interest, specifically a 14th century castle, a library with Moorish details, and the town church. There is also an interesting Parador in the town of Zafra. It's not one of my favorites because it's a hodge-podge of architectural elements, but by way of explanation it was originally a Moorish alcázar, later converted to a castle in the 15th century, then a palace residence, and finally a hotel complete with swimming pool I believe.

In the area south of Toledo, I usually try to stop in the little town of Talavera de le Reina, which is only worth visiting if you are a fan of their specialty hand-painted ceramics. (Talavera is to Spain as Deruta is to Italy if you will.) I think there are even some outlet stores right on the highway. Further south, almost into Andalucía, is the little wine town of Valdepeñas, which bottles some very respectable vintages. Last time I was there, we were given a tour of one of the vineyards, after buying a few bottles from their store.

Certainly one should carry thoughts of Don Quijote when making the drive from Toledo to Cuenca. If you actually want to see some windmills, it's probably better to map out their location beforehand, since they're still extant in only a few spots high on the plane of La Mancha. In the area around Cuenca, there is interesting geography- 1) Las Torcas, which is an area of enormous sinkholes, some dry, some filled with water. The spot is quite remote, and untouristed, except for spelunkers and scuba divers who for some reason enjoy going down in the watery holes. There seemed to be hundreds of these holes over a wide, but walkable area, although there will be lots of mud, and wild boars! 2) La Ciudad Encantada de Cuenca is a fascinating moonscape of strangely eroded rocks. My Spanish friends love to point out-- repeatedly-- that this is where the movie Conan the Barbarian was filmed. It really doesn't look like earth.

Finally, a nice stopping off place on the trip from Toledo to Cuenca is my favorite Parador in all of Spain, in the tiny town of Alarcón. The town itself has nothing to recommend, but the Parador and its siting are incredible- a castle atop a jutting promontory of rock surrounded by a swirling river. We were lucky enough to claim the very top room in the highest tower, and from our private parapet had a commanding view of the entire surrounding gorge. There are only 14 rooms, so it is best to call ahead, especially for a weekend stay. Buen viaje! Joel, in Chicago