Me and my boyfriend are visiting Spain in early October flying in and out of Barcelona. This is my second time visiting Spain (the first time was pretty recently, 2 weeks split evenly between Barcelona, Madrid (w/ time in Toledo), Sevilla and Granada) but my boyfriend's first time. We've decided to spend our time split 50/50 between cities I've visited (Barcelona & Madrid probably) and new cities neither of us have visited. What cities/towns would you recommend we visit to make the most of our time? We are open to renting a car and would prefer not to burn too much time in transit between cities. Also - we love to eat!
There are lots of great possibilities in Barcelona's and Madrid's orbits, so you don't have to go too far afield if you don't want to:
Madrid: Segovia, Cuenca (needs AVE ticket; buy early to get affordable fare), Salamanca, El Escorial. For me, Avila's not worth more than a couple of hours. The first three will more than fill a day each. If you didn't spend much time in Toledo on your earlier trip, I'd definitely recommend a repeat visit.
Barcelona: Girona, Figueres (Dali Theatre and Museum), Cadaques, Sitges. Girona's a good base if you just want to make day-trips to Figueres and Cadaques. It also works for a half-day trip to Besalu. Montserrat's a day-trip from Barcelona.
Of course, you could also head south to Andalucia (Seville, Cordoba, Granada). In that case you'd probably want to fly back to Barcelona from Granada, which argues for visiting Barcelona at the end of your trip.
San Sebastián and Bilbao are the obvious suggestions, however will involve considerable travel times to/from Madrid/Barcelona. With only 9 days (nights ??), I would look at an easy stop you can make on the journey between Barcelona and Madrid. Valencia or Zaragoza are sensible options and both perfect for a 2 night stay. Cuenca would make a good secondary stop for a single night if you choose Valencia. Alternatively, Salamanca and Segovia are easy overnight stays from Madrid.
Day
1/ Arrive Madrid
4/ To Cuenca (or Salamanca/Segovia)
5/ To Valencia (or Zaragoza)
7/ To Barcelona
10/ Depart Barcelona