Leaving in about a week for ten days in the Madrid area. Have been to Madrid before but want to see things not too distant. Plan on driving directly to Segovia. On our must see list is the Valley of the Fallen. (perhaps Escorial), Avila, Salamanca, Toledo and Cuenca. We think that perhaps Valencia is too large, too modern and perhaps not worth the miles. We like history, old towns, castles and the likes. Any suggestions would be greatly appreciated. Many thanks in advance for all your help.
If I'm not mistaken, Valley of the Fallen is still closed until further notice - has been for quite some time. EDIT: It has been closed since April 2010.
FYI - Valencia is nowhere near Madrid. A car is not needed or recommended for Toledo. If you drive to Segovia (also not necessary), then for sure stop at Escorial.
If you are renting a car and driving to Toledo I'd like to suggest a visit to the town of Consuegra. It is about 65 kilometers beyond Toledo or 135 kilometers directy from Madrid (passing through Aranjuez, also a good place to visit) and it fits in very well with your interest in smaller, historic and scenic towns. It is on the Route of El Quijote and there are several very picturesque windmills sitting on the top of the hill overlooking the town. There is also a castle/fortress there. You might combine your visit to Cuenca with the visit to Consuegra but you would probably need to stay overnight somewhere. A stop at El Escorial is a must. All of your desired destinations are great. The hard part will be to fit them all into your schedule!
Toledo You might want to take the AVE train, (1/2 hour from the Atocha Station))as parking will be a problem, but a solveable one. I have taken the train each time. Suggest the Posada de Manolo, a great hostal adjacent to the cathedral. Nice rooms, a great breakfast overlooking the spires of the cathedral, central location for all of the sites. Do not drive within the city limits (not sure that you can), so walking is the rule of the day. One of my favorite places. A one night stay minimum, recommend two. Have not been to the Valley of the Fallen, but do travel by it as it is on the way to Avilia and Salamanca. It may be closed based on other postings. Have taken the train to Salamanca (from the Charmartin Station), and it is also worth a two night stay. There is an excellent tourist bureau on the Plaza Mayor with maps, etc. Segovia is an easy day trip from Madrid. The aqueduct is the main attraction. Toledo and Salamanca will give you history overloads. almost too much to absorb, but well worth the trip!
I've never quite understood why a lot of people would want to see the Valley of the Fallen, a monument created by a dictatorial regime. Is the natural setting really special? (Thinking about it, I guess you could consider 16th-century Spain a dictatorial regime, but at least El Escorial has more history behind it).