re: Spain and Portugal-14 days

I'd suggest 4 cities instead of 5 so you aren't traveling as much. It would also give you time to take an interesting day trip out of each city.

I think Madrid and Barcelona should be definites for Spain.

The Prado in Madrid is a top-notch art museum and the food and drink scene is a lot of fun. My favorite spots were around Plaza de Santa Ana. Toledo is a quick easy day trip from here.

Barcelona is like if Florence and Miami had a kid - stay near the old cathedral and spend your evenings after dinner and too much cheap wine wandering the winding alleys trying to find your way back to your hotel. A lot of the beach towns mentioned above could be day trips from Madrid, but I haven't been to any of them.

In Portugal, I really enjoyed Lisbon. I thought the food was relatively inexpensive but tasty. If you go here, be sure to try to the custard pastries called pastel de nata and end your evening by getting a glass of ginjinha on your way back to your room.

I'd probably add Porto as the fourth stop, though I haven't been there.