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Traveling around Castile-Leon

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I am hoping to get some insight re a part of an extended trip to Spain.
We will be arriving from Porto, Portugal and have allowed a 2 1/2weeks to this section of our travels.
I am hoping to get some help with the logistics - Will rent a car to do the "outskirts" of Madrid but do not want/need a car in Madrid proper.
Madrid (4 nights?).
We wish to visit Salamanca, Avila, Toledo, Caceres, Segovia, Cuenca... other suggestions (why not, we are already overwhelmed with info).
These all look very interesting to us from reading our many tour books (mind boggling, really!).
We do not know the roads of course and love to meander BUT would like to not spend all our time doing just that. I like a couple night stays, minimum in a particular spot.

We love the history, the castles, cathedrals, monasteries, FOOD, and are hoping to experience a less touristy side of Spain.
Thank you.

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