I'm concerned that the weather might be too cold/rainy to go to Madrid and Toledo in late October. My interest is El Greco, so I'd be mostly walking to churches/museums in both cities. Your thoughts?
Sherry.....October in central Spain can be quite pleasant...temperatures in the 60s, with lots of sun. I've run into a touch more rain that you find in the summer, but nothing untoward. Wear a good pair of walking shoes...if they're leather, use "dubbin" on them to waterproof them....and carry a collapsible umbrella. Follow Rick's guide if taking the train to Toledo....it's quite a hike up the hill to the old town! You'll be overwhelmed by El Greco's work on display in Toledo and at the Prado.
if you are really looking for the indoor tourism, october would be perfect. everything will be far less crowded, and cheaper, in october. it'll be a beautiful trip!
I've been to Spain all times of the year...October is my favorite time!! Especially if you will be concentrating on the 'indoor' activities... Madrid is way tooo hot in August and the begining of september. Honestly even the beaches are not to bad in Spain in October, the water is actually at its warmest, though the beach might be a bit windy....only drawback is that many beach resorts, restaurants, bars, discos close about mid october for vacation