Valparaíso

Valparaíso spills across more than 40 hills (cerros) around a natural bay, its winding stairways and precarious streets earning the historic quarter a spot on UNESCO's World Heritage list in 2003. Before the Panama Canal opened in 1914, this was the busiest port on the Pacific coast of South America — sailors called it the 'Jewel of the Pacific' — and the ascensores (funiculars) built from the 1880s onward still creak up the steepest slopes, saving legs the climb from the flat port district, known as el plan, to the cerros above.

What the port trade left behind is a city that reinvented itself as Chile's bohemian capital: painters, poets and dockworkers turned corrugated-metal house fronts into a rolling gallery of murals, especially around Cerro Concepción and Cerro Alegre, earning Valparaíso its reputation as the country's street art capital. Pablo Neruda kept one of his three Chilean homes here, La Sebastiana, with views over the bay he loved; today it's a museum. Save room for a plate of chorrillana — fries piled with beef, onions and fried eggs — and, if time allows, hop on the Merval train for the short ride to Viña del Mar, Valparaíso's beach-resort neighbor.