I'm planning a trip to Spain and Portugal for this coming fall (leave late September, return mid-October). We'll have a little over 2 full weeks. I know that we can't "do" all of these two countries in that time, that's OK, we're not going to try. Our goal is to hit the highlights of Andalucia and a bit of Portugal (Lisbon and the Algarve).
We fly in to Madrid, and need to end (the Spain/Portugal portion of the trip) also in Madrid - after which, we fly to Morocco for a few days. From Morocco, we fly back to Barcelona, where we'll have one full day (2 nights) before our return flight to the US.
Our proposed itinerary is already ambitious, so we're going to skip northern and eastern Spain entirely (except our last day in Barcelona), skip Gibraltar and Spanish beach towns, and most of Portugal. I'm looking at just 4 days in Portugal, split between Lisbon and the Algarve.
It seems that it's not easy to string together a reasonable (efficient) itinerary through some parts of Spain, but I think I've got one sketched out that works, althogh we will be moving fast (usually every other day). It involves a variation on Rick's "take a night train to save time and money" strategy. But instead of doing a night train (which won't really work here), I'm proposing to spend a day in one city, then catch a discount flight to the next city that night (after dinner). I figure this is an efficient way to move on and utilize a few hours that might otherwise be spent having a drink or relaxing after dinner, between two cities that are not served efficiently by rail.
I've posted a map of my proposed route and day-by-day itinerary here:
http://www.interrobangmedia.com/iberia2008/
I'd be interested in hearing from others who have been through southern Spain and can comment on whether what I'm looking at here is realistic or not. My hope is to minimize the days where we move each day, keeping most stops to 2 nights. Thoughts?