Valpo-top of hill
Valparaiso is cool. It's a port, but the geography of Valparaiso generally is easy to sum up: flat bit, hills. The hills surround the flat bit, and the flat bit borders on the Pacific Ocean. Valparaiso (shortened to Valpo) was once an important seaport, but the opening of the Panama Canal had some impact on this. During its heyday, the city grew rapidly and the flat part was not enough, so homes started climbing up the hills. The hills, however, are very steep -- so steep that it's not easy to have a lot of roads connecting up and down. The solution to this was to build a whole lot of funiculars (a few of which are still in operation) to connect up and down.