It turns out Toledo is only about 30 minutes away by super-fast-OMG-we're-going-to-die train. So of course we took a day trip from Madrid.
At the train station lots of our fellow passengers began the wearying climb up to Toldeo. We, however, are devotees of Rick Steves and he gave us great advice: Beat the crowds and save your legs; take a taxi up to the square. We arrived ahead of many (but not all) of the other tourists. We headed off as the walkers and buses came up the hill.
The majority of the tourists stayed between the square, the cathedral, and the Alcázar fortress. So we hustled down the street full of shops (and a Starbucks!) to get beyond. It was lovely and quiet. We even found a guy playing bagpipes? What?
Don't get me wrong. We did go to the cathedral and the Alcázar. Both were incredible. And we shopped. And we took shelter from a surprise rain storm in the Starbucks. But we didn't go to the McDonalds or Burger King. Instead, we went to a grocery and bought bread, ham, and cheese for a "girl lunch". Yes, the ladies allowed me to participate.
We also followed Steve's guidance and took the tourist "train" around the outside of town. Embarrassing, yes, but we got a killer view of the town set on the hill that we couldn't have gotten on our feet.
We took nearly last the train back to Madrid after a full day and more than eight miles of walking. Toledo gets a big recommendation from us.