I am queen of plan/list-making and now is not an exception.
I have spent a noteworthy amount of time contemplating upon my Lonely Planet Discover Spain guide. I have flipped through (I think) every section and made notes and dog-eared the pages.
A brief summary of my plans:
Barcelona. I have already purchased plane tickets; I will be going at the very least for the weekend of September 25. I hope, perhaps, to go one more weekend, perhaps by bus. What is in Barcelona? Gaudi (a fantastical and remarkable architect) -- la Sagrada Familia (cathedral), a medieval quarter of the city, a Dali museum -- many things. Also, nearby is Montserrat, a monastery which I have seen in pictures from fellow MIT peeps in Barcelona this summer.
Toledo. About a 10-euro, 30-minute train ride away from Madrid. Cathedrals, historical stuff. Also small-ish and walkable, according to my guidebook. This trip will hopefully be happening this weekend.
Salamanca. A 20-euro train ride away. My guidebook says it is very beautiful and has a lovely town square.
Segovia. Another 10-euro train ride. It has a cathedral (I think) and a GIANT ROMAN AQUEDUCT.
Cordoba. In southern Spain. Haven't quite figured out yet quite how to get there, BUT I MUST VISIT. It has an enormous beautiful mosque with a cathedral stuck in the middle that I learned about in architectural history.
Granada. About 35 euros round-trip for a bus ticket. They have La Alhambra, a gorgeous palace/fortress thing from when Spain was under Muslim rule.
Besides these major weekend trips, my guidebook has a host of other suggestions, and I might pick out one or two, such as Consuegura (lots of windmills), Guadalupe (lovely church-y things), Tarragonia (Roman ruins), or Santiago de Compostela (beautiful church).
Not in Spain.
Paris. I am planning, hoping, planning to take a three-day weekend there September 11-13 or so. This potentially will only cost me about 80 euros (at least for the plane ticket).
(maybe) Venice. I am pretty sure this is where I would like to go for my six- or seven-day trip at the beginning of October. This is potentially a 90 euro plane ticket.
Well, that's the plan, anyway.