Cuenca or Toledo?

Toledo is the former captial of Castile, prior to Madrid.
The city is wonderful and the buildings are largely hundreds of years old.

I like Cuenca and have recommended it on this forum. It really is no equal of Toledo, however.

In addition, Cuenca is much farther from Madrid than Toledo is. To make Cuenca a practical day trip, you have to take one of the express trains. That can be very expensive (can go near 50 euros one way) if you don't buy the ticket well in advance. There used to be (and I assume still are) local trains priced lower, but they are way too slow unless you're spending more than a day in Cuenca. The express trains go to the Fernando Zobel Station outside Cuenca, from which you need to take a bus (no clue about the frequency) or a taxi into town. The train departs from Chamartin Station and takes about 1 hour. Cuenca fits very well into an itinerary that covers both Madrid and Valencia, because it is on the AVE line between those two cities.

The trains to Toledo depart from Atocha Station, which will in many cases be more convenient to the traveler's hotel. Those trains take only 34 minutes and have a fixed price of 13.90 euros each way even for last-minute tickets. You do need to be aware that tickets to Toledo are date- and time-specific, and the trains sometimes sell out. I wouldn't expect that to happen very far in advance, but Rick warns about it in his guidebook. I wouldn't plan to take the last train back to Madrid without having a ticket in hand for that train.

I think you can save a bit of money by buying a round-trip train ticket if you're prepared to commit to a specific return time.

I agree with acraven.

I’ve been to Cuenca twice; once as a day trip from Alarcón (2022) and the other we spent two nights at the Parador (2014). The walking bridge over the gorge affords a good view of the hanging houses. The main plaza isn’t huge and the cathedral isn’t as imposing as those in other cities. Continuing up the hill from the main plaza one gets a nice view of the old town and surrounding area.

I’ve been to Toledo at least six times, most recently in 2024. Our first time there was in 1978 at that’s when we visited all the towns main sites. Since then we’ve visited lesser sites. We use Toledo as a place to relax and get over jet-lag after a flight.

We always had a vehicle when we visited both towns. Of the two, Toledo would be my choice, but both are worth visiting.

Agree with above posters. We spent three nights at Parador in Cuenca (took train from Madrid, and after Cuenca continued on to ten nights in Valencia and five in Denia). Leave Cuenca for when you are Valencia-bound.

Agree Toledo is more "day trippable." But do keep lovely little Cuenca in mind for a future trip--I think it is much better with a car if you are a nature person--there are some fantastic parks and hikes in the vicinity.
But if you are looking for more outdoor activity it might be up your alley, just strolling up the street was nice--I would not compromise on travel time for it though.