This is just a little second hand trip report that I'm happy to pass along as my very busy, stressed out sister and fiancee (middle-aged) asked me to plan their trip and they have just returned with glowing reports on everything. They rented a car at the Madrid airport and drove straight to Cuenca, a beautiful medieval town hanging on a cliff about 100 miles east of Madrid.Perfect place to unwind and get into Spain.They spent 2 nights at the Parador de Turismo de Cuenca which is a beautiful renovated 16th c.monastery with breath taking views and the walk across a foot bridge spanning a deep gorge to their favorite restaurant...well,they couldn't quite find words. Next was 2 nights in Toledo but on the way there they took some side roads and visited some of the restored Windmills of the La Mancha area and also stopped at several castles perched on hills with spectacular views...often there was no one around and they were free to roam these sites on their own. Having never been to Toledo their impression of the narrow streets and distinctly Moorish, medieval aura was everything I had read posts about here in the board. They loved the Hotel el Pintor El Greco, a converted old bakery in the Jewish quarter. Location was excellent. Nice breakfast was offered and street parking was nearby where the hotelier actually walked down to the meters with them and showed them exactly what parking coupons to buy and when they needed them. I thought that was a really nice gesture as this was their first experience with the system. From Toledo they swung around to Segovia where they roamed the streets and walked up to the Alcazar. They actually much prefered Toledo. Found Segovia much more commercial and busier. They then proceeded to Madrid where they turned in the car on the Grand Via and checked into the Juan Carlos V for 3 nights. This is a historical property in the Best Western chain right on one of the walking/shopping streets and very convenient to Plaza Mayor. They said the rooms were small but very charming and comfortable, a gracious staff and nice breakfast. They felt this was a real bargain for a centrally located hotel of this quality.Well...the rest has all been said before. Lots of roaming the streets, museum visit and just sitting in the Plaza listening to the strolling minstrals.I must add they arrived the day before the national strike and the parador had a informative printout about the strike, the reasons, and it's possible ramificatons. Other than some shops being closed they did not notice much. Also that was the week of several bombings but they said they absolutely felt safe everywhere and commented about what the local news in most of our cities has to report on any given evening and found the beauty and ambience and people made Spain a perfect relaxing and interesting place to visit and they are looking forward to returning. Thanks to all for the information I gleaned from this board... they loved the trip and felt the intinerary was a perfect compromise of staying several places but not trying to cover too many miles.