Toledo or Segovia?

I thought Toledo was terrific. Great walking town and very picturesque, perfect fo. One day visit.
I cannot comment on Segovia since I have not visited.

Assuming you are coming from Madrid, Toledo is an easy, fast train ride.

I'd pick Toledo for the El Greco art, military museum, sword shops and castle.

Tough choice as Toledo is just about a given (fantastic cathedral, art, etc. etc.) but Segovia is one of my favorite places. If I could only see one it would probably be Toledo, but you can't miss no matter which one you pick.

Toledo or Segovia? You will not go wrong with either choice. Toledo is a 25 minute AVE ride from the Atocha station. You arrive at the train station in Toledo, the first and only stop. From there you can take a taxi to the Plaza Zodocover, which is the tourist center of town and work out from there. The Cathedral has a good audio guide, will take one or more hours to explore. The Alcazar holds the military museum, enter from the basement side. Excellent. The town is a walkers paradise, with many streets the size of alleys in the states leading to great places to explore.. It is better seen with an overnight, or two, stay as it is completely changed when the day tourists leave.

Segovia is a short bus ride away from Madrid. The main attraction, the Aqueduct, is seen as you approach the town. Amazing structure that gave water to the area. Up the hill you will encounter the Cathedral, one of the last Gothic Cathedrals in Spain, and down the other side of the hill is the Alcazar...royal palace...well worth a visit. The city can be explored in a day without difficulty. There are many more sights in Segovia, but these are the main.