One of the most unique cities in Chile is Valparaiso. Climbing up the sides of 42 hills, the city has a bohemian vibe that everyone loves. There are several funiculars that take you up and down various hills so that you can enjoy the view and the many colourful houses at the top. You’ll also love getting lost in the maze of cobblestone alleys that somehow magically connect all the hills. Stop in to a different “little café” every day, enjoy the street art, and in the evenings, watch the lights sparkle across the bay. This UNESCO World Heritage Site is still undergoing restoration, but even in this period of transition, the town offers incredible colour and charm. You might want to check out La Sebastiana, the former home of poet Pablo Neruda, and downtown’s Plaza Sotomayor.