I started my trip out in Madrid, and was there for three days and nights. The second day we went to Toledo.

I stayed in a more traditional area of Madrid at Hostal Corbero (which I highly recommend), near the Museo de Prado. The Madrid Vision tour bus was great. You just hop on one of its many stops. It was the first thing we did in the city and it gave us a great overview of the city, helping us learn the layout of the city and get around later on. If you just want to see tourist sites, Madrid is a really easy city to walk around. The city has a really good feel and actually does not seem like it caters that much to tourists, all considering. We expected that most people would speak at least some English, but this wasn’t the case. Most of the time, they knew only a few English words. A lot more English was spoken in the really touristy areas like that around Sol. Compared with Barcelona, a lot fewer people spoke English in Madrid.
Of the sights, we were most impressed by the exterior of Palacio Real, the great modern art collection in the Museo del R. Sophia, and Parco de Retiro. The Museo del Prado obviously has a great collection, but it’s not my favorite style. Plaza Mayor is great too, especially at night. The outdoor plazas are terrific too, especially the Plaza de Colon. Overall, two full days in Madrid was plenty for me to see all the main tourist sights. It seems like a city I could stay in for a while and try to get a feel for. People were very nice and the nightlife (which we were a little too exhausted to full take part in) was impressive. But if you are viewing Madrid as just one of many stops in Europe or don’t have a lot of time, it really does not require much time to see its main sights. For such a happening city, it doesn’t have all that many tourist sites. We actually did most of them in just one day, which isn’t that tough if you plan ahead.

On the middle day in Madrid, we took a daytrip to Toledo. The bus took about 1 hour, and then we had to take a local bus a few minutes to the city center. Not very hard to get to at all. Toledo was one of my favorite cities out of the dozen I visited all over Europe. It’s beautiful. Just go there and walk around and get lost in the maze-like streets of this walled city. I would definitely discourage going there on an organized tour. Just wander around. It’s not that big, and you can easily get to all the “main” sites as well as take in the rest of it in a day. The cathedral is one of the most impressive of its kind. Better, in my opinion, than any other I saw in Spain for sure. I also recommend the simple but beautiful architecture of one of the synagogues in the Jewish quarter. I forget the exact name, but I think it’s something like Blanco. We didn’t get to go in the Alcazar because it had just closed unfortunately. You should absolutely venture outside the walled city and go over one of the the pedestrian-only old bridges (we went over the one opposite the side where your bus will enter from). Great views of the city and the Tagus river (which surrounds the city on three sides), and very few tourists walk there. I actually didn’t find a mention of it in the three guide books I checked. Get a map or ask around to find it. Overall, this is a must-see. It has beautiful sites, terrific cobblestone streets, and is so much fun to get lost in.

If you have any questions or want more details about anything, just ask.
Adam