We decided to pass on the formal tour buses and travel to both Toledo and Segovia on our own. Service to both cities was prompt and efficient, but unless you speak some Spanish, it could be more difficult. The workers in the tourist info center in Toledo spoke limited if any English. We took Continental bus service to Toledo. It takes about one hour through an area that is not very scenic. Once in Toledo we took a ride on the "cheesy" train ride from Plaza Zocodover around the city. This train travels outside the city and across the river to provide absolutely fabulous views of old Toledo. If you don't have a car or if you are not on a formal tour then this is the only way I could envision making such a view possible unless you take a cab. Tickets can be purchased at the tourist info center adjacent to the Plaza. Highly recommended. Narration is a tape in both English and Spanish. If you have some basic ability to speak and understand Spanish then this is a great way as you can spend as much or little time as you like at the various sites.
Bus service to Segovia was via La Sepulvedana. The bus station in Madrid was well worn, but functional. The tourist info center in Segovia at the base of the aqueduct was staffed with very helpful folks who spoke good English. DO NOT miss out on seeing the palace La Granja san Ildefonso which is a short bus ride, perhaps 8 miles outside of town. You catch the bus at the same bus station in Segovia. Cost is two Euro round trip. You are dropped off about 100 yards from the entrance to the palace. This has been called "little Versailles" and the gardens as well as the palace are spectacular. Even more appealing, the place was virtually deserted compared to other sites. The locals at the bar indicated that there is little if any tourist traffic during the week. If you make the trip to Segovia, don't miss this palace.
It appeared that the employees at the bus station speak no English. Therefore, you may want to consider a more formal tour to these cities if you don't know Spanish. If you can speak some Spanish then strike out on your own. Remember, part of the adventure is making your own pathways.
Both Contiental and La Sepulvedana have good websites where you can check schedules ahead of time. For convenience, the web addresses are posted below. These are in Spanish. Have a great trip!!
http://www.continental-auto.es/index.do http://www.lasepulvedana.es/ Powerhouse