Like San Francisco, Chile’s historic Pacific port is a child of the California gold rush, as a major seaport on the passage around the Horn. Also like San Francisco, it has so many hills  that a walking tour of its streets, steps, and winding footpaths can be as productive a cardiovascular workout as a lengthy session on the StairMaster.
For those who tire of walking, more than a dozen funiculars —the functional equivalent of San Francisco’s cable cars—lift Porteños (as Valparaíso residents are known) from the downtown financial and commercial districts to their hillside neighborhoods.
Declared a UNESCO World Heritage Site for its unique urban geography, Valparaíso is undergoing a real-estate renaissance as the values of its distinctive traditional houses—Victorian-style structures clad with calamina (corrugated metal)—rise as steeply as the hills themselves. It still has some drawbacks: While trash collection has improved with the placement of dumpsters at certain key locations, this has driven Valparaíso’s numerous street dogs into other neighborhoods where the trash is still left in plastic bags for collection. The streets, alleyways, sidewalks, and staircases are dappled with canine soretes—watch your step or wash your feet.
Valparaíso’s rundown port, the city’s least attractive area despite two kilometers of prime ocean frontage, is undergoing an overdue privatization and modernization of its docks to improve their handling capacity and tourist appeal. In addition, construction of a new southern access route has reduced heavy truck traffic through downtown’s congested core and is opening the shoreline to the public.
Except for suburban commuter rail, transport in and out of Valparaíso  is exclusively by bus; though LAN (Esmeralda 1048, tel. 0322/251441) sells tickets and confirms reservations, Santiago is the nearest commercial airport.