Madrid vs. Toledo?

I recommend at least one over night in Toledo, two if you can make it. The city is different in every way when the last train of tourists heads back to Madrid. Great hostal - Hostal de Manolo, almost adjacent to the cathedral, in the center of all you will want to see...and has a great breakfast overlooking the Cathedral. Segovia is interesting, but a day trip is all that is required. The three main sites are The acqueduct, the cathedral, and the alcazar. Madrid: The Prado, The Park Retrio, The Royal Palace, Plaza Mayor....

My preference is to limit my time in Madrid. Madrid is a new capitol, with about as much history as Washington DC (NY, Boston, Philadelphia, Baltimore, etc. are all older cities with more history). Madrid also has about the most expensive (and least enjoyable) lodging and food in Spain. I love the Prado in Madrid, because it's a world class art gallery. Madrid has nicely planned green spaces (because it's a new city). I also enjoyed Temple Debod (but that's really Eqyptian history transplanted to Madrid).

Cordoba, Segovia, Toledo (really anywhere in Spain) offer authentic medieval town centers as well as cheaper and more comfortable lodging. If you're driving, I'd probably plan to see the walls of Avila on your way to Segovia. Segovia is definitely worthwhile, it offers an aquaduct, a cathedral and a castle within a short walk. The castle is sometimes panned as being a fanciful restoration (true of many European castles) but is worth a visit and has a nice collection of medieval armor. A very short drive, but maybe too far to walk, out of town is a church (Iglesia de la Vera Cruz) that dates back to the Knights Templar.

Toledo was our favorite "twisty road" medieval town in Spain. I spent more time in Madrid because there is more to do, but I enjoyed my time in Toledo more.

Hmm... Madrid became the Capital of Spain in 1561 and it is believed it was founded in 860 AD

Since Columbus didn't sail the ocean to find the new world until 1492 and the Pilgrims didn't settle in what would become the US until 1620 I am not sure the "Facts' presented above by Brad are correct As for 'expensive' lodging. I have five nights for $218 ... not sure how much cheaper it can get LOL! (And yes, it's in a Hostal but it gets great reviews and looks nicer then the Europa where i stayed last time so..)

And while he didn't love Madrid I do and plan to spend 7 days there this fall so... you really just have to decide what appeals to you.

Forgive Brad, he is being a little harsh. Madrid is the newest of all Europe capitals and was never a walled city like many others so it has not had the time to built an extensive history. But it is still worth a couple of days but not over going to Segovia, Avila, and Toledo.

I spent a week in Toledo and would've enjoyed more time – it's an amazingly well preserved city, fascinating cathedral, wonderful early buildings, and much El Greco (admittedly, not a plus for everyone). Avila is a wonderful walled city, and I really enjoyed 3 days there. Four days was more than enough in Madrid; I would have been fine moving on after 3 days.

See that's the difference, I can't imagine spending more then a night or two in Toledo. It's nice at night but during the day it's more of a zoo overrun with tourists IMHO LOL! But, I love Madrid.

I think you really just have to read and look to see what appeals to you . Watch the shows on both destinations, read some travel guides, I even search on line for trip reports and read them.

When I let myself get swayed by others is when I wind up spending way too much time someplace others thought was just wonderful, but didn't fit me.

Try to find a balance. Although you wouldn't want too many one-night stays in a trip, our tour groups have sometimes spent one night each in Toledo and Segovia, which could leave you three in Madrid. (Now, the tour does Segovia as a day trip from Madrid, but that change had more to do with other driving/timing issues.)

What Carol mentions, being swayed by others reviews, is why I really like traveling without reservations. I have a good idea where I'm going to stop and prepare a list of potential lodging for all those places before my trip - but I like being able to say, "Let's stay an extra day," or, "Let's move on," as I'm traveling - rather than being locked in.

She is right that each of us has our likes and dislikes. Mine are medieval history, art (up to impressionism), music, culture, eating local (not fancy) food and meeting people. The big cities have the art galleries and museums (and often medieval centers), but the smaller towns are where you will meet locals and learn about their culture.