Michelle, 2 ears ago in mid-September my wife and I did the same trip, only flying into Lisbon and out of Barcelona. A quick rundown of what we did: Flew into Lisbon, arriving Saturday afternoon; spent two nights there and picked up a rental car in downtown Lisbon, then drove to the Algarve (Salema, Rick's favorite) for one night. We then spent a night in Saville. From there we had lunch in a white hill town in Andalusia, then on to Tarifa for 2 nights so we could take the ferry to Tangier for an 8-hour tour with Aziz, one of Rick's tour guides. We then drove to Gibraltar for several hours, before staying for 3 nights in Nerja on the Costa del Sol. Nerja is the only town Rick likes on the coast, and it is wonderful. From there we drove up to Toledo for a night, then into Madrid, where we turned in our car. Stayed in Madrid for 1 1/2 days, then splurged and went first class with a sleeping compartment (with bath) on the overnight train to Barcelona. 2 nights there then home.