Hubby and I are taking a day trip from Madrid in September and would like to take a later train (to arrive right before 11am), is 5 hours enough time to walk around and have a meal to just see another city with no real agenda? or how much time is recommended? If we book a later train 5pm and then determine we are done earlier, could we jump on an earlier train back? Please share experiences.
What will take time is if you visit museums and the cathedral. Simply walking around only takes a couple hours. I enjoy looking at the Alcantara Bridge. My favorite bridge however, is San Martín partly because it is pretty and there’s a legend attached to it. Likewise, there is a legend to the Bitter Well (pozo amargo) near the cathedral.
The historic center is a mile from the train station. There is an escalator just past the Bisagra gate that takes one from the lower town to the upper town if you’re walking.
In 2024 we stayed at the Parador just outside of town. We spent a couple hours just walking around the historic center. Had we never been there before a few more hours would have been nice. We’ve been to Toledo at least six times since the late 1970s, never as a day trip, so others who have only been there once could probably give you a better estimate of time needed for wandering.
You can certainly do it in 5 hours (plus the time for the train trips).
The cathedral should definitely be on your list to see. I could spend hours in that cathedral alone, but I think you could do it in less time. The Alcazar is fascinating, and a wonderful spot for another 1-2 hour visit to see military history and artifacts. We've never made it over the El Greco museum but that's another popular site.
Taxi drivers picking up at the train station will offer (for a price) to take you on a "highlights" driving tour out to the Mirador del Valle (the overlook site across the river that you see on all the postcards), then drop you in the center of the tourist area (e.g., Plaza de Zocodover).
It is an understandably busy day trip spot, so there's a reward to those who fan out from the central areas and explore more of the lanes.
We stayed the night for the first time on our most recent visit and found the town gets very quiet (in March at least) after sunset. It gives an interesting contrast to see the town without its normal day trip rush. Wandering the Jewish Quarter after dark was a lovely way to see some of the "old city" feel. That may not be possible for you to stay over night, but staying later in the day probably helps filter out most of the tourist crush even in September.