Just two hours northwest of Santiago is the port city of Valparaiso. It was built on dozens of hills right at the ocean's edge and is basically a cartographer's worst nightmare. The streets curve up the hills like snakes, and everywhere you turn there are narrow, graffiti-adorned stairways that wander off... somewhere. There's really no such thing as a direct route in Valparaiso, just lots of urban adventures.
The city is full of color, with brightly painted buildings, crumbling Spanish architecture and gorgeous street art on every surface imaginable.