Ninety minutes northwest of the Santiago Airport and right on the Pacific Ocean, Valparaíso, Chile sprawls up and over 43 hills in a South American version of San Francisco. The entire city is a UNESCO World Heritage Site, slowly being rescued from a moldering state of elegant decay, its buildings painted like a cross between an outdoor art museum and a basket of Easter eggs.
Requiring sturdy walking shoes and a willingness to keep your eyes open to detail and design, an exploration of the winding streets, funiculars, harbor, seafood and architecture here was one of my all-time favorite urban adventures.
Soon after 1818, when it gained freedom from Spanish rule, Valparaíso beefed up its navy, expanded its port, and positioned itself as an ideal stopover for ships traveling between the Atlantic and Pacific Oceans. By the mid-19th century, it was attracting European immigrants and shipping magnates, as well as American business fueled by the Gold Rush.
Drop-dead gorgeous buildings went up all over town, with the port-adjacent Plaza Sotomayor at the center of the action. Here in the flat expanse of town called El Plan, you’ll find one of the city’s finest structures, the robin’s-egg blue Edificio de la Comandancia Naval (Naval Command Building), bursting over most of a city block.
In the wake of the Panama Canal, Valparaíso’s fortunes began to decline in a graceful crumble. However, the stone streets, harbor breezes and historic details of the central city are still worthy of a wander. Abandoned buildings are covered with murals and high-toned graffiti, and business cooperatives and artists’ studios are moving into former mansions. Hop on a historic trolleybus to tool around the flatlands and see how modern-day Valpo (as it’s known to locals) bustles amongst political monuments, municipal buildings and funky neighborhood joints.
Just a block off the Plaza Sotomayor, the Port of Valparaíso is a mix of teeming metropolis, shipping-container flotilla and Fisher-Price marina. Between the salty characters, enormous sea lions and even more enormous container ships, you could easily entertain yourselves by simply hanging out at the docks across from the Customs House.
If you’d rather get out on the water, though, you can hire a tugboat driver for about $10 and a smile. If English doesn’t work, try the following question in Spanish: “¿Puede que nos llevará en un viaje en barco?” (Can you take us on a boat ride?)
A half-hour ride will give you a more orienting perspective on the hilly layout of the city, its forest of new construction, and even the adjacent seaside resort town of Viña del Mar. Your outing might come with a guided tour, but be advised that this can be far from a trained-docent situation; if you end up the captives of a droning shpiel, feel free to turn away and do your best to glide along the harbor in silence.
To get up into them thar hills, the most direct way is to take one of the ascensores (elevators) dotted around town. Around the turn of the 19th century, there were about 26 ascensores in Valpo, but these days there are more like 10 running at any given time.
Simultaneously antique and oft-mantained, these historic funiculars generally cost less than $1 and will spare you hoofing it up some of Valpo’s steepest climbs. I took three ascensores in a single day, and each one offered a different, exciting view of the city.
I also did a lot of walking, and I’d recommend that you do the same. Cerro Concepcíon, Cerro Polanco and Cerro Alegre (cerro loosely translates to “hilly neighborhood”) are especially full of winding streets, doorways and staircases that are covered with street art. While these outdoor installations aren’t formally sanctioned by local government, they’re still encouraged as cultural enhancements; in other words, in areas where renovation efforts are slow or non-existent, murals and creative tagging are seen as the next best thing.
I found some of my favorite street art while scaling Cerro Concepcíon’s steep, winding Calle Cumming — and in a cool book called Street Art Chile — but I’d have also loved to book a 3-hour tour with Valpo Street Art Tours. I always like the idea of meeting local artists and hearing about their motivations.
Whether you’re wandering in a pair or with a group, just remember to occasionally watch where you’re stepping. There are adorable, sleepy dogs all over the place, but few people think to clean up after them.
And if you’re already on the Calle Cumming, keep going up to the city’s most famous cemeteries: Cementerios Nos. 1 and 2. Number One is the open-to-the-public “dissidents” or immigrants’ cemetery, and is full of fascinating tombstones that tell a tale of shipwrecks, disease and far-flung locales, while the more private Number Two is arguably a bit more elegant, its focus on native-born Chileans. Both offer sweeping hill views and a rounded sense of Valpo’s 19th-century heyday.
Nearby in Cerro Carcel, take yourselves for a stroll around the Ex Cárcel Parque Cultural, a museum/gallery space/community center/art school/theatre/public park carved from the site of a former fort-turned-prison. Possibly a more exciting development for locals than tourists, as green space and formalized cultural pursuits are as yet scarcely found in Valpo, this is still a fun place to poke your heads around. You can check out a community greenhouse, take part in interactive art installations, and eavesdrop on ballet and circus classes.
A couple of hills away, my favorite neighborhood was the Art Nouveau-heavy Cerro Alegre. My boutique digs here, the fire-engine red and art-filled Palacio Astoreca Hotel (review to come), opened in 2012 after a full-scale renovation, in keeping with the preservation focus of the entire area.
Just next door on the Paseo Yugoslaveo, the equally spectacular Palacio Baburizza has been restyled as the Museo de Bellas Artes (Fine Arts Museum). The Chilean and European art displayed here is more soothing than exciting, but the building is definitely worth a visit for it romantic architectural details and dreamy sea views.
The Cerro Concepcíon had my favorite views, for its mix of street art, calamina (corrugated iron) construction, and especially wild colors. Rising above the fray is the 1897 Igelsia de la Santa Cruz, a two-tone green German-Lutheran church that was renovated in 2011. There are lots of hostels and small hotels up this way, as well as a wide array of bars and eateries.
One of the most popular restaurants in this area is Cafe Turri, largely due to its stunning city-and-ocean view, but also for its delicious mix of European recipes and fresh local ingredients. Head out to the terrace for some crusty bread, shareable salads and gorgeous seafood dishes — and maybe even a pisco sour.
Later in the afternoon, you might want head back over to Cerro Alegre for a treat at Amor Porteño, a cozy little heladeria full of teapots and bird art. Resting my feet on the vintage, hand-painted tiles while mainlining some hazelnut gelato was a delightful way to reboot my sightseeing mojo.
Consider sticking around the Cerro Alegre for at least one evening, too. Enjoy some Chilean wine and cuisine while surrounded by wine boxes and local artwork at funky little Cafe Vinílo, or turn the night into a special occasion at the creative, intellectual and tongue-in-cheek Alegre, the Palacio Astoreca’s sophisticated on-site restaurant.
If you find yourself craving a little post-dinner nightlife, check out this list of venues. Or, entertaining yourselves can be as easy as taking a walk: choosing any direction will take you along stone-paved streets towards twinkling city lights, whimsical street art, and a magical sense of being very far from home.