El Escorial, Avila, or Toledo

With one day I would do Toledo. With two I would add Segovia. But all are good choices. Enjoy

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I agree that for a one day trip Toledo is ideal and Segovia is also a great second choice.

Overall I would choose Toledo as a stand alone day. It's a little too hard to combine it with El Escorial.
El Escorial is much better done as part of a day to Segovia.
Avila would trail as my third choice.

Toledo would be tops for a visit and will fill an entire day (and more if you had the time). It's easy to get to by high speed AVE from Atocha Station in Madrid (or by bus). Lines can be long at Atocha so it helps to by the tickets a day or so beforehand so you can just show up and board the train. You can get the round trip ticket then or at the Toledo station when you are ready to return.

El Escorial is a half day trip or more and is reached by bus. I like it but would have it on the list only for a longer Madrid stay or a second or third Madrid visit.

Segovia is also nice, a notch below Toledo with an impressive Roman aqueduct and great old town. Also a full day visit and easily reached by high speed AVE train.

Have not been to Avila but it gets nice reviews; but again is probably a 2nd or third visit destination.

El Escorial and Toledo are nearly in opposite directions so it makes it hard for a one day trip. Go with Toledo.

We did a day trip to Toledo last September, wonderful.
Tip: if getting train tickets at Atocha, make sure you line up in the right area & then line (Hoy=today). We encountered 3 different areas selling tickets for specific routes. Staff were helpful pointing the way after we asked as most signs were Spanish only. Ticket booths (4 out of 7) selling advance tickets had barely a customer but did not help out the huge lines for day tickets so if you can, get your tickets the day before if only to ease the stress. Secure your return tickets as trains fill up fast. You can always change it at no cost if there is room on an earlier train. We missed out on the 10:20 train because of the lines, leaving on the 11:20 train, returning on the 17:25. Enough time for a quick lunch and an overview of Toledo.

The tourist train in Plaza Zocodover takes you across the river for spectacular views of Toledo. Well worth the few euros as I don't know how you'd get there on your own.

Definitely Toledo...don't miss it!!

Toledo is my choice as well...25 minutes from Atocha in Madrid and you are there. The tickets have the car number and seat number printed on them. A good ride. When you arrive in Toledo there are taxis at the station. Take one to Plaza Zodocover...the main square. A tourist office is about one half block off on a side street, away from the restaurant side. Get a map and begin walking. The Cathederal is down the hill, allow one - two hours with the hand held audio guide. Worth it.

From Plaza Zodocover, go through the keystone arch (easily seen) and turn left at the bottom of the stairs. You will see the Museum on the right as you cross the street...again worth the visit. Directly in front of you is a great restaurant, partly on the street (it is a deadend)...good food.

The Alcazar, big building on top of the hill, contains the military museum...enter from the bottom. Great exhibit.

The Jewish quarter is very good. Also the St. Tome churchl

Marika wrote: The tourist train in Plaza Zocodover takes you across the river for spectacular views of Toledo. Well worth the few euros as I don't know how you'd get there on your own. There is also a local bus that takes you across the river and up to a good sport for the spectacular view. Ask at the TI. There's one across from the Cathedral and they were very helpful.

I'd choose Toledo first. Lots to see and do, great medieval city with narrow twisty roads.

Avila has a great wall view from a place called four posts, walking the wall is decent as is the Cathedral. After that, there's not too much to see in Avila.

I didn't choose to see El Escorial. Like Madrid, it's a little too new for my historical tastes. If El Escorial seems to your tastes, I'd suggest Aranjuez as a possible alternative. It's Royal Palace is a smaller version of El Escorial (same era) plus a really nice garden and, I believe, smaller crowds.

The three sites really represent very different eras in Spanish history, so I think it's important to consider what period most interests you.

I spent a week in Toledo and it wasn't enough time (but I really love El Greco). I enjoyed 3 days in Avila, partly devoted to the religious sites associated with St Teresa of Avila and St John of the Cross. Three days was a good amount of time there. I would rate El Escorial third, and do it as a partial day trip from Madrid – after I had done everything else in Madrid that interested me.

For a day trip, Avila will probably be much less crowded than to Toledo, but it's also farther away.

I didn't think I would like Toledo as much as I did. If you are interested in Spanish history, the Military History museum in the Alcazar is quite good. They even have a small section about the Spanish Civil War--which many other history museums avoid since it is still such a hot topic.