Valparaíso is a city of two parts: El Plan, the congested, flat commercial district closest to the sea; and the 42 cerros (hills) that rise up steeply behind it.
Valparaíso's hills defy even determined cartographers. Av Almirante Montt and Urriola lead from El Plan to Cerros Concepción and Alegre. From Plaza Aníbal Pinto, Cumming takes you to Cerro Cárcel; from nearby Av Ecuador, Yerbas Buenas winds up Cerro Bellavista, accessible from the other side by Ferrari. Av Alemania winds along the top of the more central cerros.
Valparaíso Map (www.valparaisomap.cl) is by far the best map of this notoriously hard-to-navigate city, while Ascensores de Valparaíso (www.ascensoresvalparaiso.org) has an interactive map of the city's old lifts. Look for print maps at hotels and tourist information kiosks.