Not all beautiful is skin deep. Such is the case of Valparaiso, a World Heritage site 90 minutes by bus northwest of Santiago. Gritty and weathered from head to toe, it is a city which does not immediately make you swoon at first sight. On one of her 42 cerros - hills jutting straight from sea, its slopes filled with crumbling mansions and colorful buildings and rickety funiculars - I stood while a blanket of fog rolled in from the Pacific. I was only here for a day yet after a few hours, I began to like its rugged and bohemian core.

Getting to Valpo - as locals fondly call the city - required an early start for me. I was joining a free walking tour at 10 AM with Freetourvalparaiso. This meant leaving downtown Santiago while my hosts where still asleep, hopping on the Metro (the second biggest in South America after Mexico City) to Pajaritos where I transferred to one of the many buses regularly leaving the terminal. Roundtrip fare was about 3,500 CLP (or almost 7 USD).

Santiago's bus terminal in Pajaritos
A foggy view of Valpo's port with Turri Clock poking out among commercial buildings below

Getting off at the bus terminal in Valpo, I realized I only have a few Chilean pesos left. I asked around in my halting Spanish where I can change US dollars. Someone pointed me to a hardware store where an elderly gentleman arose from reading his morning paper and conducted the monetary exchange. Armed now with more Chilean pesos, I showed him Valpo's map, pointing to where I intended to go and asked if the little buses or micros outside will stop at Plaza Anibal Pinto - starting point for the walk.

When I heard "Si", I felt fine taking the small bus which was the equivalent of only a few American cents. While I could have just walked along Avenida Pedro Montt, taking about 40 minutes, I wasn't so sure if I'd make it to the plaza in time. Besides, I haven't even eaten breakfast yet. So I joined the throng of locals heading to the more chaotic part of city.

Ten minutes later, I got into the plaza, saw this man wearing a distinctive "Free Tour" red jacket and approached him. Antonio introduced himself as the walking tour guide. "Oh please, take a breakfast first", he intoned, pointing to one cafeteria in front of us. "Walking for the next three hours with an empty stomach isn't a good idea".

Once done with a quick brekkie, I saw Antonio was already in the company of 9 other Valpo visitors - a merry mix of Americans, Brits, Aussies and one Taiwanese. Two stray dogs wagged their tails, acknowledging Antonio's familiarity in their turf. "Don't be scared, this one's Chulo. He always accompanies me in my tours", Antonio said. Chulo walks with a limp, a testament to his daily struggle with other stray dogs.

Freetourvalparaiso's  itinerary on this 3-hour walk covers pretty much the major sights, involving some decent leg work going up and down stairs and steep sidewalks. Shortly after leaving Plaza Anibal Pinto, we encounter Ascensor Reina - one of the city's remaining working funicular railways (also called elevators) which connect El Plan (the coastal strip) to the hilly parts of town. Built in 1902, it felt so old and creaky, not to mention a tetanus threat, as we went up on a short ride uphill.

From our first vantage point looking down on this semi-organized chaos of urban planning, we could see what Pablo Neruda meant when he wrote a poem in her honor, telling us of her "disheveled hills". Colorful houses seem to elbow each other out on steep hillsides. Street art fill every nook and cranny as if walls were meant to convey freedom of expression. It's a crayola world with a grungier, edgy approach.

One of Valpo's cobblestone streets

While our view of the harbor was cloaked with fog, there's no denying Valpo's attachment to maritime trade. In mid-19th century, ships plying the route between the Atlantic and Pacific stop by her port. It was around this time when European immigrants also settled in, bringing along with them, among many things, their architectural tastes. The opening of Panama Canal in 1914 and the transfer of wealthy families to Santiago marked the decline of Valpo's golden age.

From one cobblestone paseo to the next, we continued trekking, up and down we went, past more walls filled with hallucinogenic street art. We got down to busy Ave. Esmeralda and gazed up at the main office building of Diario El Mercurio - the oldest Spanish newspaper still in publication today. Nearby is another historic building housing Latin America's oldest stock exchange.

Valpo's colors
Diario El Mercurio headquarters

Then we rode on Ascensor El Peral, another funicular railway. The noisy grunts we heard couldn't hide its old age. It brought us thankfully in one piece. Up there on Paseo Yugoslavo, the Palacio Baburizza looked radiant having been restored after years of neglect. On clearer days, the paseo commands spectacular harbor views.

We went down through stairs exploding with graffiti, emerging on a calle which steeply sloped towards Calle Pratt before leading us to this wide square called Plaza Sotomayor. Dominating the plaza is the Edificio de la Comandancia Naval (Naval Command Building) while on the other end is the naval war-related Monumento a los Héroes de Iquique (Monument to the Heroes of Iquique).

Ascensor El Peral

Our walking tour ended right at the busy port. After handing Antonio a tip for a job well done, I decided to do some more exploration. The Taiwanese visitor - who works as an English Literature professor in Taipei -  tagged along when he realized we both have the same plans. Never mind if one Taiwanese fisherman got killed in Philippine waters at the time - we didn't let that get in the way of enjoying some more walk (as if the last three hours were not enough).

We cheated a bit by hopping on one museum-worthy trolleybus that's been moving people since 1952. The ride was soon over as we got off at the junction where a cobblestone road led up Cerro Bellavista. We huffed and puffed, stopping just in time to admire some more quirky street art and catch our breath. The higher we go, the lesser the quality of street art has become - more like the work of some newbie still learning a thing or two from those in the lower side of the hills.

Naval Command Building on Plaza Sotomayor
Valpo's trolleybus looks just like it did in the 1950s
Pablo Neruda's former home

At the top of Cerro Bellavista is La Sebastiana, the former home of Chilean poet Pablo Neruda. Like his La Chascona home in Santiago, this is just as unusual as it looks. Having only seen the outside of his Santiago home, I decided on just resting my sore feet on a bench in his garden while my new Taiwanese friend explored La Sebastiana's interiors.

From the hilltop, we separated as I made my way down to Calle Pedro Montt and walked all the way to the bus terminal. Feeling so hungry now, I followed my nose to nearby Cardinal Market where vegetable and fruit vendors spilled unto the street. Shoppers idled on their way, blocking paths as they sized up huge tomatoes and carrots and apples straight from boxes. Stalls selling meat and sausages assaulted my nose and so I made a quick escape, eventually finding a table at one random restaurant whose local patrons were glued to 'futbol' aired on TV.

Lunch for me is not usually this late at 3:30 PM but thinking about what I've seen in Valpo, I was just so happy devouring meat from the parilla. There's no need to rush now, I told myself. The bus bringing me back to Santiago was a mere short walk away.


  1. wow what a wonderful experience. free tour. i really really like to see chile someday, i hope it comes true.

    off topic, what company did you use for your alaska adventure? did you do the train to denali and stayed in denali?

  2. There are many cities offering free walking tours (tips are of course appreciated) so I always take advantage of it when I see one. For Alaska, my camping trip was organized by Get Up And Go adventures. We did not stay in Denali.

  3. Oh Dennis, your photos reminded me of the time I went there, in 2011! I loved that city, going up and down the cobblestones and riding the elevators! Thanks for bringing back memories!

    1. Hi Jeruen, I did read your post about it. I remember you had a local showing you around as well - an opportunity which makes the visit all the more memorable.

  4. Love the artistic vibe of the place. There's so much color!

    1. This profusion of gritty art is what I think sets Valpo apart from all other colorful cities I've seen.

  5. Such a colorful, lively place. I'd love to see it one of these days. And your photos are stunning. :)

    1. Thanks Wander Woman! Hope you do make it there one day - it won't bore you I promise :)

  6. Hi Dennis,
    Sounds like you had a nice, colorful day in Valparaiso. It looks pretty much as I remembered, but paints look fresher. (I also remember the tons of stray dogs everywhere.) You'e right, Valparaiso's beauty is beyond sin deep. Beyond it grittiness lies a charming, soulful city. Lovely photos.

    1. Thanks Marisol! I remembered the guide saying every now and then some artist gets commissioned to do another painting on top of an older painting which I think is pretty much what happens with street arts sanctioned in other big cities.

  7. i think i could endure hunger and fatigue (but not thirst and necessary bladder breaks) from uphill-downhill walk and would take my lunch even at 4PM just to see those pretty street arts that reminded me of andy warhol. best part, the walking tour is free! it's rare here in asia (at least in penang, sinagpore and manila) to find a free heritage walking tours. lucky you to got that chance in valpo and even luckier to have extra time to do your own exploration.

    the colors of valpo are so alive on your photos! great captures as usual!

    1. It was good exercise going up and down those hills docgelo! There are now many countries offering free walking tours, including many parts of Europe so I always join them whenever available. Of course, tips are expected.

  8. Great that despite the news, you and the Taiwanese got along pretty well.
    Looks like a great place to exercise. Love the colors and the art!

    1. We've actually exchanged e-mails and has mutual open invitations to visit each other one day - see what travel can do?


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