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Valparaiso, Chile

Chile’s main port city is geographically fascinating. In the winding streets and steep hills of its colorful neighborhoods, it exudes a gritty, Bohemian vibe.

We arrived in Valparaiso (“Valpo”) after a short, two hour bus ride from Santiago. A beautiful, sunny afternoon punctuated the town’s colorful buildings. We made our way to the top of Playa Ancha Hill and checked into Casaclub Hostel. A backpacker haunt clearly looking to be more of a hip hangout with its swanky lounge music playing.

After settling in, we quickly set out to explore the neighborhood. Passing through scenic Plaza Waddington, we picked up fresh veggie empanadas at La Piazza, then made the descent into downtown.

While the hills are primarily residential, el Plan (“downtown”) is where most public and commercial buildings reside. The area is flat and easy for walking. In Plaza Sotomayor, the town’s main square, we took in exquisite heritage buildings and lively cafés. During our time in Valparaiso, something was always going on here. On one occasion, a forklift pushed around a huge 18-foot puppet of a mustached man with glasses dressed in a suit. We assume the Charlie Chaplin like figure was perhaps a beloved cartoon character? Another time, a group of fearless performers of all ages climbed on top of one another to build a castell – a human tower. Amazing and terrifying.

A visit to Valparaiso wouldn’t be complete without enjoying the fresh seafood.

Heading to the waterfront to seek out Mercado del Puerto, we discovered it had closed due to a recent earthquake. Nothing but boarded up restaurants and stray cats and dogs (of which Valparaiso has many.) Plenty of hawkers tried to lure us into their restaurants. Avoiding the tourist trap, we instead made our way to Restaurant Montserrat, a local eatery we’d passed earlier. Here, we enjoyed fried seafood empanadas and paella de mariscos, a hearty seafood stew. Best of all, we got complimentary pisco sours – very cheap and charming!

Later in the week, we had another memorable lunch at Restaurant Aires Porteños. With the dining room’s floor-to-ceiling windows, we were able to look out onto the waterfront below. Dining on ceviche (seafood cured in citrus juices) and fried merluza (hake fish), we watched those same restaurant hawkers outside chase after potential patrons. Pure entertainment.

Having an elevated vantage point is one of the best ways to experience Valparaiso.

Past the walls of graffiti and the town’s infamous street art, we headed for the hills once again. We chose to forego one of the town’s many funiculars and instead, climbed up what seemed like an endless staircase. Finally, we reached Cerro Concepcion and Cerro Alegre, the town’s most iconic hills. We spent hours wandering the crooked streets of these neighborhoods, marveling at the different colored homes. Even in areas where the houses weren’t as nice, the vibrant hues gave off a fresh, optimistic vibe. The variety was spectacular. It’s as if no paint store would dare sell the same color twice. Truly amazing how a simple coat of paint can transform grit into instant happiness. 

Pasaje Templeman and Paseo Atkinson are a couple of Valparaiso’s most picturesque streets. On display are tidy rows of upscale rowhouses in a rainbow of colors. Many feature miniature front lawns with idyllic picket fences. Bright bursts of bougainvillea and blossoming flowers add to the charm. Hotel Brighton is particularly striking with its vivid yellow facade and black and white checkerboard patio – the ideal place for a cocktail over sunset. We opted for an ice cream cone from Helanderia Josefina Grau instead, enjoying it in a park overlooking the bay.

Despite the carefree nature of our meandering, we did have to be careful where we went.

A few locals actually approached us to tell us to avoid walking in certain areas and helped us figure out a safer route. Like other countries in South America, petty crime can be a problem in Chile – best to avoid any questionable areas whenever possible. We appreciated these kind-hearted souls looking out for us. We encountered this in other places as well like Montevideo, Uruguay and Buenos Aires, Argentina. Unfortunately, our luck ran out in Rio de Janeiro, Brazil… ironically, our last stop in South America.

In any case, we enjoyed our time in the ramshackle town of Valparaiso. A real working port town combined with a thriving art scene, set in a remarkable setting that’s as discombobulated as it is beautiful. When trying to describe the feel of this place, it’s as if the hills of San Francisco mixed with the colors of Cinque Terre, the grittiness of Crete, the Bohemian vibe of Granada and the artistic flair of Mexico City. In short, Valparaiso is its own thing.

Chilean poet-diplomat Pablo Neruda said it best:

“Valparaíso, what an absurdity you are, how crazy: a crazy port. What a head of disheveled hills, that you never finished combing. Never did you have time to dress yourself, and always you were surprised by life.” 

Pablo Neruda

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