Day Trip from Madrid - Segovia vs. Toledo

I don't think you can do wrong with either. Both towns are charming, historic, and easy to navigate.

I have enjoyed both Segovia and Toledo on many trips
Segovia has three main attractions. The aqeduct (spelling?), the cathedral and the Alcazar. The first you can see as you walk by, the second is a great gothic cathedral, and the last is a palace. All are walkable, up the hill and down the hill and lots of streets, buildings and people in between.
Toledo has its cathedral, several museums, and the other churches. I personally enjoy Toledo more for a one time visit. Even though it may be more crowded, there is more to see and to do in the city. Check out the web sites for both places. You will not go wrong with either choice.

Toledo unless you are really into Roman history. Segovia has an amazing aqueduct and is a charming town, but other than that, its sights don't compare to those in Toledo (the Alcazar is a late 19th century reconstruction).

Toledo has so many layers of history and culture. It has some Visigothic ruins, Moorish architecture, two Jewish synagogues (both in the Mudejar style) and of course Catholic Reconquista history and architecture. Even the Alcazar there was an important site in the Spanish Civil War. And while crowded during the day, is an incredibly charming town to explore (get off the main paths and the crowds go away). And there are El Greco works if you are into art.

I've been to both. I'll add a vote for Toledo over Segovia. Both are nice, so you'll do well with whichever you pick.

Both are easy day trips from Madrid- Segovia is more charming compared to Toledo IMO. Segovia is connected nicely by Septudelvana bus and Toledo by lovely AVE fast train which gets you there in 30 minute. You wont go wrong with either choices.

Toledo is one of my favorite medieval cities. It has a ton of sights and history and is the most easy to reach from Madrid. The hardest thing about Toledo is deciding which sights to see in a day trip. I'd stay a night or two, IMO it's better than staying in Madrid (not to mention cheaper).

Segovia isn't as great as Toledo but it has an aqueduct, Cathedral, old center, and castle all within a walk-able area. I enjoyed the armor display in the castle. Just outside the area is a Templar era church, a little too far to walk to. I thought it was interesting but it's small and probably not worth a taxi trip for most people.