Hi, newbie!! With two weeks, I think that your "tentative" itinerary may require more moving than you will enjoy. I'd begin by picking up a car at Barajas Airport (Madrid), drive to Segovia (we like sleepy Turegano as a base), continue south to "conquistador" country, i.e. Extremadura (Trujillo/Caceres), on to Sevilla (park the car, you won't want it!!) through the pueblos blancos to Estepona then Granada, followed by Toledo and Madrid. This might be a little longer than a two week trip but you'd see a lot. Ending in Madrid is a real treat as you'll be so well acquainted with the Spanish way of life that you will truly enjoy the big city (which really doesn't seem so big once you realize that you can walk or go everywhere on the Metro). You could drop your car off at the airport to make things easier (downtown locations are difficult) or at one of the railway stations. We rent from Auto Europe which provides good rates and no charge for dropping off at other locations. Please, e-mail me if you have additional questions. If you're more interested in the north and central areas, I have a great three week itinerary (you could revise it) with wonderful places to stay/eat/etc.--Carole