Segovia or Toledo

We have taken day trips to each of them and much preferred Segovia with it’s history than
Toledo which we didn’t care for anywhere near as much as Segovia.

I also preferred Segovia because I had never seen an aqueduct.

I liked both cities a lot. Although the aqueduct is by no means the only worthwhile sight in Segovia, it's the one with the most visual impact. Numerically speaking, Toledo has a lot more sights, and they're scattered around a huge and atmospheric medieval district; it just doesn't have that one sight that's as big a "wow" as the aqueduct. I favor Toledo because I'm a big fan of Mudejar architecture and love wandering around medieval lanes, but I wouldn't discourage someone who really likes Roman ruins and/or engineering marvels from choosing Segovia. Note that if you don't buy your train tickets ahead of time, you could end up paying over 70 euros for round trip tickets to Segovia, whereas Toledo will always cost about 22 euros. (Those trains to Toledo can sell out, though.)

Both are good choices. Toledo is my wife’s favorite town in Spain. The aqueduct in Segovia is still very impressive. To me, the main sites in Segovia are the aqueduct and Alcázar. Toledo, I feel, has more museums and historical sites to see. Which you choose depends on what you want to do while there.

I love them both and spent 2 nights in each. That being said, if you only have a day trip, I might choose Segovia, simply because it seems easier for a day trip. Toledo would have felt rushed to me to try in only a few hours.

You really could just flip a coin, if you have time for only one, and not miss out. Both are great, each has their own charms.

Segovia has some Roman history, a neat castle, a nice church with a town square, and pig centric cuisine. The transport options are a bit better, or at least no worries of sold out trains.

Toledo has more art (El Greco), again a spectacular church, better than Segovia, a nice town for wandering, a bit of the Spanish Civil war history, and the food, while meat centric, seems a bit more varied than Segovia. Transport is easy, just buy round trip, maybe even a day ahead.

Both offer views from a town perched on a hill, both can be touristy.

Segovia seemed more unique with the aqueduct.

Try to do both, but if you have to choose, I'd go by this: Wait until you are actually in Madrid and get the weather forecast. Especially if you care about photography, but even if you don't, go to Segovia if it is a bright, sunny, blue sky day. Walking around looking at the aqueduct and alcazar will amaze. If the weather is expected to be cloudy, gloomy, and grey, go to Toledo, where almost all the major sights are indoors. See the cathedral, the El Greco museum, the Museum of Santa Cruz, etc. You won't care if it ugly outside because everything inside is beautiful.

We did both. Both are great, but I would say if you choose, pick Toledo.

Thanks so much everyone for sharing your valuable insight! It’s so helpful. Happy holidays!