Of course the answer to the title question is “Yes.” If you have time, you should visit both. But when researching our own Spanish itinerary we saw so many people asking the question on various message boards that we thought we’d wade in with our own take.
Both Segovia and Toledo are medieval, walled cities that are within a 30-minute high-speed train ride away from Madrid. Which one you choose really comes down to what you’re looking for, how long you have to visit, and, if you’re on a very tight budget, how much you have to spend.
Everywhere Once 