Originally Posted by
SASfan
Viña del Mar has been compared to San Francisco, while Valparaíso is more like Oakland.
Excuse me? That's antipodal to my experiences.
Valparaiso is San Francisco - hilly, artsy, with a big Tenderloin not so nice district at the bottom of the hills that you really don't want to spend much time in. Lots of cool streets, funky shops, old restaurants.
Viña del Mar is like San Jose, or some crappy beach town. Modern, characterless, ugly. Things are safe but bland.