I'm starting to look into a first trip to Spain and Portugal next September. Since I plan it all myself, I like to get started on brainstorming before the end of the year. We'll probably be gone 3-4 weeks (more time in Spain) to perhaps 8-10 locations. So far, I've only looked at RS's top recommendations, so this is very rough and flexible. Please let me know what you think of these locations or feel free to suggest others. We like a variety, so some historic old towns, beachy areas, and mountains or some other type of terrain as appropriate. My husband is great about driving, but ideally, we'd like to only drive 4-5 hours at a time and stay 3 nights (though an occasional a one-nighter when appropriate). We usually like to wind down a bit toward the end but finish in an interesting location.
Fly into Barcelona?
Madrid - at least 6 hrs away, so maybe fly or train and then pick up a car there?
Granada
Sevilla
Hill towns around Arcos de la Frontera and Ronda?
Day trip to Tangier, maybe sleep in Tarifa?
Drive to southern coast of Portugal
then Lisbon
Return home from Lisbon?