Madrid side trips

Most of humanity (it seems) does Toledo as a day trip from Madrid (virtually every organized bus tour of Spain does that, and even most non-tour independent travelers do it too, because it looks and is easy). So if you want your day in Toledo to be shared shoulder-to-shoulder with all of humanity, then go for that out-and-back, packed-with-tourists, super-crowded, mid-day day trip along with everyone else.

If, on the other hand, you're not looking for the "too crowded to enjoy anything" experience, spend the night in Toledo, and enjoy the beautiful and magical old city when it's at its best, in the quiet evening and early morning hours, with few other tourists in the way.

I like the vibe of Segovia, and have stayed there on separate trips. The aqueducto is phenomenal, and the castle, but if you have time for only one side trip, Toledo could be justifiable.

For us several years ago, Toledo was just a day trip, also we didn’t stay the night. Be prepared for more up and down hiking than in Segovia. Did not see the armory inside the castle - it was more a City of El Greco day for us.

I’d still lean towards Segovia myself (55% vs. 45% for Toledo), but if you’re already leaning towards Toledo (55% or more), that would make for a very good side trip.

I spent multiple nights in both towns and would be glad to return to each of them. I'd put Toledo higher on the priority list simply because of more sights. I'd say the same thing even if you hadn't had earlier opportunities to see aqueducts, though I admit the one in Segovia is stunning.

There's no wrong answer here. Madrid just has more than its share of fabulous towns in its orbit. When you return you can visit Cuenca, Salamanca and Alcala de Henares.

The mention of Toledo here often elicits mention of how impossibly crowded it can be. I have no reason not to believe that may be some people’s experience. But I was there on a sunny weekday in mid-November, and that wasn't my experience at all. I enjoyed it very much as a day trip.

Thank you all. This is helpful input. I look forward to visiting Spain in September ;)

We were recently in Madrid and one of our day trips via regional train was to Cercedillia. Great little village with access to nice hikes…. if you need/want a break from crowds/cities!

Madrid has arguably the best day trip possibilities of any major city in Spain. Spending a night in Toledo is a time machine to the middle ages, highly recommended!

Other potential Madrid day trips -
Royal Palace of Aranjuez
Chinchón
Cuenca
Archeological Park of Segobriga
Archeological Park of Reccopolis
Zaragoza (also worth an overnight!)

Zaragoza looks amazing. That might be a quicker trip from my stays in Barcelona.
Thanks for all the suggestions. I think there will be more than one trip to Spain for me ;)

Happy to help! I'd make the case that Zaragoza can also be a practical day trip from Madrid. Zaragoza is in fact only a 1:20 hr ride on the AVE high speed train from Madrid.

It's just a 15 min walk from Zaragoza's train station to the Aljafería Moorish Palace, and then it's only another 15 min walk to the Casco Antiguo (old town) grab lunch there, and then visit the Basílica del Pilar in the afternoon and catch the AVE back to Madrid in time for dinner.

The recently introduced AVLO low-cost highspeed train also makes the trip from Madrid to Zaragoza with tickets starting at €7.

Zaragoza is a very worthwhile destination. I have two cautions, though: It positively bakes in the summer, and the train/bus station is in something of a food desert. I assume there's a place to buy a sandwich at the station, but in 2016 I saw nothing on my way to the Aljaferia. That sort of mattered because I was staying at the Eurostars hotel at the station, and its business was so slow in the summer that it closed its restaurant; there were minimal selections available from room service. (I didn't travel to Spain to eat frozen pizza, but the cheese plate was OK.)

Zaragoza would make a good day trip. We recently spent two nights there. Personally I was disappointed with the Aljafería other than the main entrance and garden. The rest was empty rooms with little resemblance, as far as Arabic script on the walls, to places like the Alhambra or Alcázar in Sevilla. The ceilings were pretty as were a couple doorways. I’m glad we got the retired person rate.
Cuenca is nice. Its historic center is small and one can see all the sights in a short amount of time. The hanging houses and pedestrian bridge over the gorge are the main draw, as well as the small cathedral. Chinchón has a pretty plaza mayor but little else. Its castle is closed to visitors. A couple hours in each is sufficient; longer if you have dinner.

Toledo! should be your first pick. when are you going? i was there in early april and it was not crowded at all.

As of 2016 Cuenca had a couple of good modern-art museums. I haven't checked to be sure they're still open, but I'd be surprised if they were not.