Growing up in Miami, the idea of dropping temperatures and changing leaves and snow was so foreign and seemed to me, this idealized image that I desperately wanted to be a part of, especially as my own family was falling apart when I was a kid, with my parents' extremely contentious divorce and both of their subsequent mid-life crises where I was caught in the middle. It's not an uncommon scenario, by any means, especially for the late 70s/early 80s, but for a kid like I was, introverted and shy to start with, those carefree images amidst falling leaves or frolicking in the snow, were powerful icons. Symbols of everything I thought my life was lacking.
After growing up in South Florida I was shocked to go to college in central Ohio and see white clapboard houses and picket fences and deciduous trees and chimneys smoking and all that Leave it to Beaver stuff.
I had fairly dim notions of Paris until I read Tropic of Cancer and Anais Nin's diaries. That's what made me want to go to Paris.
When I first got to London I was pleasantly overwhelmed reading the Underground map and seeing all these places I knew from songs by the Stones and the Kinks. There's Knightsbridge! There's Notting Hill! There's Shepard's Bush!
But Peter Pan's flight over London at night was my first real sense of London. Or possibly any city.
My first impressions of Berlin were from a Rolling Stone article about David Bowie and Iggy Pop living there in exile. (I've always found it horrible and funny that Bowie had to leave Los Angeles and go to Berlin because LA was too decadent.)
I guess my New York was from reading the Village Voice in high school. That's the NYC I wanted to see.
Risky Business made me think that riding the trains in Chicago would be a very sexy undertaking.
At some point in my post-collegiate life I think I realized that I had very deficient notions of world geography and started to rectify that with a fascination about port cities. Which is why I know Valparaiso is on the coast and Santiago is inland.