Toledo or Segovia?

I like both, but I'd choose Toledo without a doubt.

Me too, and it would be ideal to spend the night in Toledo in order to enjoy the town without all the other day trippers, or at least stay into the evening and enjoy dinner and an evening stroll.

Me three, and the evening in Toledo is magical, so do stay over if you can.

Toledo imo.

You actually can do both. In 2016, we and another couple took a day tour through Tripadvisor leaving Madrid around 7:45 am by bus to Toledo. Once there, our guide took the group (about 25 people) on a walking tour of the town; and at the end we had about an hour free time to further explore a bit aka shop. We then hopped back on the tour bus and onto Segovia. Upon arrival, we were given a few recommendations for lunch, for which all of us were on our own. After about an hour, we then met up and took another guided walking tour which included entry to the Alcazar. We arrived back in Madrid in time for dinner. Granted, this was a whirlwind tour of both cities, but you will get a flavor of each.

Another vote for Toledo.

I wouldn't want to split a day between Toledo and Segovia; the two cities are on opposite sides of Madrid. Aside from the fact that Toledo has enough to keep a traveler busy for more than one day, there's the issue of how much of the day would be devoted to transportation. A round-trip train trip to Toledo takes just a bit more than 1 hour. Traveling Madrid-Toledo-Segovia-Madrid by bus would be about 4-1/2 hours--over three hours wasted sitting on a bus.

Just because it's physically possible to set foot in Toledo and Segovia on the same day, that doesn't mean one should do so. Sometimes it really is better to say, "We'll get there next time."

Loved Segovia but a vote here as well for Toledo.
Lovd it so much we are going back this summer while we'll be in Madrid for the first time.

Like the others, I love both, but if forced to choose I’m another vote for Toledo. I’m also in agreement with the comment about not trying to see both in the same day. Enjoy and experience the place you choose and don’t rush it.

My vote is Toledo too- more to offer, but nevertheless Segovia is charming too.

Another vote for Toledo. I was in Madrid in 2015 and was able to do a day trip each to Segovia and Toledo. If I had to do it over again and remove one from the itinerary it would be Segovia. As others have said Toledo has more to offer. We even enjoyed the tacky tourist "train" tour that goes around the outer perimeter of the city. Buen viaje!

No question in my mind....Toledo, Toledo, Toledo...I plan on a day trip to Segovia in early May when we are in Madrid... I also plan a trip to Toledo overnight from Madrid. If I had to choose, Toledo always wins.....it is magical and the cathedral is my favorite in Spain.