Valparaíso, or "Valpo", feels like no other city in South America. Colourful houses are stacked on more than 40 hills above a working port, connected by stairs, alleys and old wooden funiculars, and almost every wall has a mural. It is chaotic and a bit run-down, and plenty of the graffiti isn't art, but that's part of its character. Keep in mind that it's a city to walk slowly, up and down, so bring comfortable shoes.
History & How Long to Stay
The bay was home to the Chango fishing people when Spanish captain Juan de Saavedra arrived in 1536. For almost three centuries it was a small port, until independence and the 19th century turned it into the most important harbour on the Pacific coast of South America, a compulsory stop for ships sailing around Cape Horn. British, German, Italian and French merchants built banks, mansions and churches on the hills, and the city had the first stock exchange in Chile and El Mercurio de Valparaíso, founded in 1827 and the oldest Spanish-language newspaper still in circulation. The funiculars were built from 1883 so people could reach their homes on the hills. A huge earthquake in 1906 and the opening of the Panama Canal in 1914 ended the golden age, and the city slowly declined. In 2003 its historic quarter became a UNESCO World Heritage Site, and since 1990 the National Congress meets here. Fires are a constant threat on the hills; the one in April 2014 destroyed nearly 3,000 homes.
How long to stay: 2 days (one full day at least).