Valparaíso

Valparaíso's geography — a flat port squeezed against a wall of steep hills — made the city genuinely difficult to navigate on foot as it grew through the 19th century, and the solution was a network of ascensores, wooden funicular elevators built starting in the 1880s to haul residents between the port and the residential neighborhoods above. At their peak, dozens operated across the city; around a dozen still run today, more surviving historic funiculars than any other city in the world, and several remain genuine daily transit for residents rather than tourist novelties.

Cerro Alegre and Cerro Concepción, two of the most visited hills, hold the highest concentration of Valparaíso's dense, constantly evolving street art scene — building facades, staircases, and even utility boxes covered in murals ranging from political commentary to pure abstract color, dense enough that UNESCO specifically cited the city's unique urban and artistic character when listing its historic quarter as a World Heritage Site in 2003.

Pablo Neruda, Chile's Nobel Prize-winning poet, kept a house in Valparaíso called La Sebastiana, one of his three Chilean residences, chosen specifically for its sweeping views over the port and hills — visitors can tour the house today, preserved with much of Neruda's original eclectic collection of maritime and folk art objects intact.

The port itself, once one of the most important stops on Pacific shipping routes before the Panama Canal's 1914 opening redirected traffic away from the long journey around South America's southern tip, gives Valparaíso a genuine maritime history distinct from Chile's more inland, mountain-focused identity elsewhere in the country.

The city's steep, maze-like streets and famously chaotic-feeling layout — a deliberate contrast to Santiago's more orderly grid — reward slow, unplanned wandering more than a checklist itinerary, and most visitors who spend real time in the hills come away describing Valparaíso as one of the more genuinely surprising cities in South America.