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You don’t have to be in great physical shape to explore Valparaíso to the fullest, but it helps. Micros and colectivos (diesel-belching buses and “group” taxis) and creaking ascensores (funiculars, a type of cable railway used on steep inclines) notwithstanding, “Valpo,” as it is known, affectionately or derisively, depending on who’s using it, is a walking town and the most intriguing neighborhoods—and jaw-dropping vistas—are “up there” on the steep hillsides.

Facing west over the not-very-passive Pacific, Chile´s principal port city curves around its maritime stage like a massive amphitheater, hugging a bustling bahía (bay) of the same name. Sturdy wooden fishing boats with melodic names like Reina Elena vie for anchorage among hulking freighters flying flags of nations representing six continents—and the odd ice-breaker capable of visiting the seventh. Most of these ships can readily face the sobering challenges of the southern oceans; others are bereft of even paint, unabashedly exhibiting vast orange patches of ominous rust. Beyond the inner harbor, the gray silhouettes of Chilean (once British) naval vessels lie sheltered by the southern curve of the bay.

The broad Avenida Errázuriz—named for an accomplished Chilean citizen of the mid-19th century—sweeps along the waterfront, this costanera (coastal road) the aged port’s definitive border between the dockside activity and city’s sea-level structures. Unenlightened architecture of the latter half of the 20th century towers arrogantly over squat English and Spanish rococo of the 19th century, their incompatible façades permanently darkened by the ravages of the Pacific’s fickle weather. Behind them, eastward, the rest of Valpo clings to its mountainsides. Indeed, the first sunlight of the day doesn’t begin to brighten most of its narrow, meandering streets until late morning. Tired, dour villas of the once-wealthy and the brightly painted ramshackle homes of the modern poor sprawl with blind faith in their foundations on the ridges and in the shallow valleys of this uncommon urban labyrinth.

Stepped sidewalks, slippery footpaths and impossibly narrow streets zigzag everywhere (Valpo men extol their women as having the best legs in Chile. Well muscled, surely, but most shapely is debatable). Entryways to homes and shops, churches and eateries are located at every imaginable level of the structure. To enter the front door of one tidily maintained home, you must cross a short, sturdy scaffold to a tiny porch hovering over a drop of a hundred meters or more. Adventuresome visitors who do not get lost at least twice a day among the 28 or so cerros (hills) of Valpo are not true urban explorers.

More than a dozen ascensores—literally “elevators,” actually “funiculars” dating to the late 19th and early 20th centuries—climb the steep slopes of the various cerros from the city’s centers up into a myriad of neighborhoods. Local legend has it that there was widespread suspicion of devilry in the clattering, rickety contraptions, much of the unsophisticated populace regarding them as some kind of un-godly route between hell and heaven. This fear was dispelled when wives of local officials were persuaded to board the dark wooden cabins, one at the top of the short route and another at the bottom. As they passed one another mid-way, the motors were stopped and the ladies enjoyed tea together, exchanging prerequisite gossip through the tiny windows. The naysayers were duly hushed.

During the heady years of early independence, Valpo was transformed into the young nation’s commercial and financial center in which English expatriates played an integral role. Spurred by obscene wealth flowing from the northern nitrate mines, Chile’s first banks were established here—among them A. Edwards and Co. and the Bank of London—as was its first stock market. The obvious legacies of Spain notwithstanding, the influence of 19th century England emerges throughout this singular city on the cerros.

Plaza Victoria, the “nucleus of elegance” at the turn of the last century, is today one of its commercial and social hubs and Paseo Atkinson, a narrow plaza on Cerro Concepción, is a popular gathering place for young people. The imposing Iglesia Anglicana Saint Paul, by engineer and architect William Lloyd, still holds services as it has since 1858. Once-grand mansions of the city’s long-departed elite grace Avenida Gran Bretaña that curves around the flanks of Cerro Playa Ancha, Valpo’s easternmost hillside. And perched prominently overlooking the docks, the Hotel/Restaurant/Pub Brighton reigns with premier accommodations.

All along Valpo’s narrow waterfront “downtown,” the past is omnipresent, not only visible in its eclectic architecture, but evident among its enduring enterprises, most of them highly revered, a few huddled in shadows of ill repute. Among the former are the venerated restaurants: the Bar Cinzano, the Café Riquet, the Café Turri, the Casino J. Cruz M., all half a century old or more. When the breeze is right, the dishes of the day are revealed by their aromas that waft out onto the sidewalks to mingle with the salty smell of the ocean.

Late into the night, alluring strains of the bolero and the tango serenade patrons who may sit for hours undisturbed, whether savoring a multi-course dinner or simply sipping a tiny cortado (coffee). The musicians and singers may be almost as old as the establishment in which they play, but their passion for the melodies and lyrics is quietly exhilarating.

Incongruously, perhaps, Valpo is rife with post-secondary school institutions, particularly for the arts. Young people appear everywhere, gathered in doorways along narrow streets or around park benches in shaded plazas. They listen to a promising musician or sing along, draw or paint an obscure building, scribble lines of poetry in a well-worn notebook. Indeed, renowned Chilean poet Pablo Neruda found inspiration in Valpo for several years.

As the sun sets behind the horizon of the southern Pacific, the panorama to the east is one of its reflections in 10,000 windows shimmering across a vast mosaic of brightly colored facades of toy-like buildings terraced high into the evening mist.

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