The best city to visit is one in which art, history and geography have intertwined to create an energetic, self-defining metropolis that owes little to the influences of other urban centres. The port of Valparaíso Chile, is one such place, a veritable San Francisco of the Southern Hemispherec —as hilly and foggy as its North Pacific brother, but smaller, funkier, and lacking in the latter's wealth-driven glitz and commerce.
Chilean poet laureate Pablo Neruda, who famously faced his writing desk here toward the Pacific, also famously penned the sonnet "I love Valparaíso." It's a sentiment shared by many who visit this seaside enclave, but a two-and-a-half-hour drive from the capital of Santiago. You can bus or train but it's worth it to drive coastward cross the Central Valley, stopping at organic vineyards like Emiliana along the way. A once-booming port, Valparaiso fell into disuse when the Panama Canal altered world-shipping routes in 1914. Today there's still commercial shipping and fishing, and the bustle of Chile's extensive navy, but only a quarter-million residents enjoy the precipitous streets of European architecture and an explosion of outdoor art — a melding of mural, poster and graffiti the likes of which exist nowhere else. There's only one way to see both historic and creative sides of Valparaíso, and that is to walk its charming streets.
Where to begin? Well, Fundación Valparaíso has done the job for you, laying out a 30-km walking tour broken into thematic stages. Known as the Bicentennial Heritage Trail, each stage takes approximately one to three hours, and a guidebook provides historical, architectural and anecdotal information. Not to worry if you find yourself with nose so buried in the guidebook that navigation becomes difficult, Fundación has placed arrows on the street for each stage. It's better not to be rushed, but the reality is most visitors are making a one-day detour from Santiago. If you likewise have limited time, the following tour from seaside to a hillside highpoint will net you the finest overlooks and attractions. A couple of provisos: avoid Mondays because most museums and restaurants are closed; and the route can be quickened by swapping some of the nastier climbs for scenic rides on the city's iconic funiculars.
Begin at Prat Pier. If you prefer viewing the city like a wide-eyed sailor arriving for the first time a century ago, take a cheap, 20-minute boat ride around the bay in a rustic fishing skiff. Otherwise browse the curio shops along the dock.
Leaving the pier, cross Errázuriz to reach Plaza Sotomayor. The sea once lapped the edge of this plaza, where gates of the blue-and-white neoclassical Naval Command dominate the west side. Here, heroes of the 1879 War of the Pacific that pitted Chile against a Peru-Bolivia coalition are buried beneath a large monument. Chile's victory resulted in it taking possession of the mineral-rich north, cutting Bolivia off from the sea (a sore point to this day) and extending the country's size by nearly a third. Learn more about the war in the Naval Museum.
To the left of the plaza, next to Palacio de Justicia, ride the Ascensor Peral funicular to the summit of Cerro Alegre and famous Paseo Yugoslavo, named by nitrate baron Pascual Baburizza (a Croatian), who built the lovely terrace walkway. Here also is Palacio Baburizza, where the baron lived until his death in 1941. Constructed in 1916 with the best European Art Noveau handiwork, the Palacio is today Valparaíso's Fine Arts Museum, housing a collection of Chilean and European paintings and free admission. The entire Cerro Alegre area, including the museum, is currently being renovated. Emblematic of this upscaling is the Hotel Palacio Astoreca that will open its doors in October 2012. The resplendent 1920s-era Victorian mansion is now a 23-room hotel de charme offers luxury accommodation, chic spa, gourmet restaurant, and utterly breathtaking views of both urban landscapes and Valparaíso Bay.
Continuing along Paseo Yugoslavo the road curves to the right around a tiny plaza to Calle Alvaro Besa, which uncoils down the hill (a shortcut is Pasaje Bavestrello, a cement stairway at the left). By now you're seeing wall art aplenty. Cross Calle Urriola, walk 25 metres and turn left into another narrow stair, Pasaje Gálvez, which corkscrews past the colorful facades of some of the city's most aesthetic homes. At Calle Papudo, climb the stairway and turn left into Paseo Gervasoni, another promenade featuring a row of stately 19th-century mansions.
Along the walkway is Casa Mirador de Lukas, dedicated to the brilliant, much-loved cartoonist and satirist who worked for the newspaper El Mercurio. There's a small admission price but it's worth a look. After, stop for coffee at venerable Café Turri.
Continue around Gervasoni until you reach Calle Papudo then head southeast to Paseo Atkinson, another stunning pedestrian walkway bordered by homes with zinc facades and British-fancy guillotine windows. Continue down the pedestrian stairway until you reach Calle Esmeralda and the end of the walk. You can also descend by doubling back and riding the Ascensor Concepción funicular to Calle Prat.
Either way it's time for a Pisco Sour (the national cocktail) in any one of a dozen cozy cafés. Or maybe two.