Toledo - walkable

The historic center is up on a hill. There is an escalator if you didn’t feel like making the walk. To me, it is very walkable and not overly large. I’ve always felt perfectly safe.

Yes and yes. As noted above, the part of the city you will want to investigate is up a real hill from where you will presumably arrive (by train). Take the escalator up unless you are looking for a good leg stretch. If it's hot out (and it often is), you'll be glad for that escalator.

The old center is compact and easily walkable (lots of cobblestones, though, so take care if your ankles are not up to uneven surfaces). While the compactness helps minimize the distances, it also tends to concentrate the crowds, which can get pretty thick in high season. Those crowds are the reason many suggest that Toledo is best done as an overnight stop, rather than a day trip (because nearly every tourist in Spain does Toledo as a day trip, which means day-trippers all share a small space with vast numbers of others; for a better experience, go spend the night and the beautiful old city will be empty and charming in the hours after/before the day-trippers roll in).

There are plenty of things you want to see as a visitor that aren't right in the corridor between plaza Zocodover and the cathedral , not least of which are the Victorio Macho museum and both synagogue-museums, which are walkable but everything is uphill in both directions no matter where you start in Toledo.

Toledo was our first two nights in Spain, flying into Madrid. Our hotel was near the synagogue museum. We took a taxi from the train station; otherwise, we walked everywhere. We did take the little tourist train (which we never normally do) since it takes people along a route outside the city for the beautiful panoramic view of the city.

It has been a number of years but we took a bus from Madrid and it dumped us on the corner of the square without having to walk to the top of the hill from the train station. The last time I posted this, someone said that the bus how goes to the train station. So you might check at the bus station in Madrid as to where the bus stop is in Toledo. Once on top the hill it is pretty flat. The evenings are very nice since most of the tourist go somewhere else.

@Jean, can you tell me more about the little tourist train?
Thank you all, I will be overnighting in Toledo.

Here’s some photos of it. It is one of those corny tourist trains, but this one will give you some great views. Plus they stopped at the panoramic viewpoint, so people could get out and take photos. I had read ahead of time to sit on the right side of the train since the route goes the direction where the views are all out that side.

https://www.tripadvisor.com/Attraction_Review-g187489-d3226914-Reviews-Toledo_Train_Vision-Toledo_Province_of_Toledo_Castile_La_Mancha.html

I’ll go ahead and add my trip report since you will be there overnight:

https://community.ricksteves.com/travel-forum/trip-reports/1st-time-to-spain-trip-report

The tourist train is well worth it. Yes, it's touristy, but so what? It's a lot of fun and the views are spectacular. You won't see these views if you arrive in Toledo by train from Madrid. So definitely take the tourist train!

I took the tourist train too. It sounds corny but as already noted it's well worth the ride for the wonderful views. Parts of the city need minimal up/down walking. Some bits are San Francisco hilly.

Allow time to admire the beautiful train station on arrival or departure.