One of the first Chilean cities founded by the Spanish, Valparaíso was South America’s most important port for hundreds of years, until the inauguration of the Panama Canal. Declared a UNESCO World Heritage site in 2003 for its architectural and cultural significance, “Valpo” is one of Chile’s most interesting cities. With bohemian cafes, artists’ workshops, boutique hotels, and colorful homes spread across its dozens of hills, you’re sure to find a suprise at every turn of the winding streets.