Valparaíso's dramatic topography—45 cerros, or hills, overlooking the ocean—requires the use of winding pathways and wooden ascensores (funiculars) to get up many of the grades. The slopes are covered by candy-color houses—there are almost no apartments in the city—most of which have exteriors of corrugated metal peeled from shipping containers decades ago. Valparaíso has served as Santiago's port for centuries. Before the Panama Canal opened, Valparaíso was the busiest port in South America. Harsh realities—changing trade routes, industrial decline—have diminished its importance, but it remains Chile's principal port. Most shops, banks, restaurants, bars, and other businesses cluster along the handful of streets called El Plan (the flat area) that are closest to the shoreline. Porteños (which means "the residents of the port") live in the surrounding hills in an undulating array of colorful abodes. At the top of any of the dozens of stairways, the paseos (promenades) have spectacular views; many are named after prominent Yugoslavian, Basque, and German immigrants. Neighborhoods are named for the hills they cover. With the jumble of power lines overhead and the hundreds of buses that slow down—but never completely stop—to pick up agile riders, it's hard to forget you're in a city. Still, walking is the best way to experience Valparaíso. Be careful where you step, though—locals aren't very conscientious about curbing their dogs.
Valparaíso has an inordinate number of nocturnal establishments, which run the gamut from pubs to tango bars and salsa dance clubs. Thursday through Saturday nights most places get crowded between 11 pm and midnight. Young people stay out until daybreak. The main concentrations of bars and clubs are on Subida Ecuador, near Plaza Anibal Pinto, and a block of Avenida Errázuriz nearby. Cerro Concepción, Alegre, and Bellavista have quieter options, many with terraces perfect for admiring the city lights.
Outside of Santiago, there are more shops in Valparaíso than anywhere else in Chile.
If it's handicrafts you're looking for, head to the bohemian neighborhoods of Cerro Concepción and Cerro Alegre. There are dozens of workshops where you can watch artisans ply their crafts.
Paseo 21 de Mayo
Ascensor Artillería pulls you uphill to Paseo 21 de Mayo, a wide promenade surrounded by well-tended gardens and stately trees from which you can survey the port and a goodly portion of the city through coin-operated binoculars. A gazebo—a good place to escape the sun—seems to be hanging in midair. Paseo 21 de Mayo is in the middle of Cerro Playa Ancha, one of the city's more colorful neighborhoods.
Valparaíso's most impressive square, Plaza Sotomayor, serves as a gateway to the bustling port. Comandancia en Jefe de la Armada, headquarters of the Chilean navy, is a grand, gray building that rises to a turreted pinnacle over a mansard roof. At the north end of the plaza stands the Monumento de los Héroes de Iquique, which honors Arturo Prat and other heroes of the War of the Pacific. In the middle of the square (beware of traffic—cars and buses come suddenly from all directions) is the Museo del Sitio. Artifacts from the city's mid-19th-century port, including parts of a dock that once stood on this spot, are displayed in the open under glass.
People come to La Sebastiana to marvel at the same ocean that inspired so much of Pablo Neruda's poetry. The house is named for Sebastián Collado, a Spanish architect who began to construct it as a home for himself but died before it was finished. The incomplete building stood abandoned for 10 years before Neruda finished it, revising the design (he had no need for the third-floor aviary or the helicopter landing pad) and adding curvaceous walls, narrow stairways, a tower, and a polymorphous character. A maze of twisting stairwells leads to an upper room where a video shows Neruda enunciating the five syllables of the city's name over and again as he rides the city's ascensores. His upper berth contains his desk, books, and some original manuscripts. What makes the visit to La Sebastiana memorable, however, is Neruda's nearly obsessive delight in physical objects. The house is a shrine to his many cherished things, such as the beautiful orange-pink bird he brought back embalmed from Venezuela. His lighter spirit is here also, in the carousel horse and the pink-and-yellow barroom stuffed with kitsch.