We took a day trip out to the colorful port city of Valparaiso from Santiago. In some ways, Valparaiso is similar to San Francisco: they are both hilly port towns, have similar architectural styles reflected in their hillside houses, both benefited from trade for the California Gold Rush (before the Panama Canal was built, ships stopped here on their way to San Fransisco), both were severely damaged by earthquakes in 1906 and both have cable cars to get up various steep hills within the city.
Valparaiso is a rough and somewhat seedy working port and naval town. It seems like how San Francisco may have been in the early 1960s or late 50s. There is a big artist community here, and the buildings are colorful , with various murals and drawings on many of the buildings, in addition to lots of graffiti.
We had great seafood at a big open air market, and then took a quick tour of the town. We went up two different cable cars to get some great views of the port and the various colorful neighborhoods with odd little hillside buildings. Valparaiso is a UNESCO listed town and is definitely worth the quick trip from Santiago.