From Santiago, I took a Pullman bus to Valparaiso. It’s a gritty port city, filled with steep winding streets (like Lombard Street in San Francisco), and A LOT of stray dogs. You can take stairs up and down the hills, but there are also funicular railways (like Pittsburgh) to help simplify the trip. I used one of them to reach the Mirador del Cerro Artillery, from which you get really splendid views of the entire port, and of the neighbouring city of Vina del Mar.
In Valparaiso, I stayed in at the lovely Hostel Caracol, where I met a couple of hilarious German women who were on a really great bike trip around Chile. The hostel atmosphere was great, and the city was filled with lots of hidden secrets, including a fantastic live music scene. I’m not sure if this relates to the end of Pinochet’s rule in the 90s, but Chile seems to have a healthy appetite for hard rock and metal. Awesome.
I was only in Valparaiso for one day before heading back to Santiago, and on to Buenos Aires. Although my time here was short, I enjoyed the city and was able to see many parts of it by walking through the various parts of town. My advice: watch for the dog poop. With all the strays, it is plentiful.