You can’t visit Valparaiso without exploring its not so beautiful parts. The continual juxtaposition between old and new, pretty and ugly, peeling paint and brilliant works of art, give Valparaiso a fascinating contradictory twist and feel. Of course, it can be difficult to ignore some of the unpleasantries of a big port city such as the rundown, falling apart streets, the garbage, the sticky smells, the dog poop and the residual grime. But this is what makes Valparaiso all the more interesting.

One such place where you will truly see some of Valparaiso’s startling contrasts is in El Plan (the commercial district) and the port where the history of Valparaiso began centuries ago. Today, it remains the central hub of activity with congestion, traffic, noise, dirt and all the things you’d expect to find in a major seaport. This area is remarkably different than the lovely Cerro Alegre and Concepción just a ten to twenty minute walk away. Yet it is a must-see part of town in order to get a full understanding of Valparaiso.

As we headed down to El Plan after lunch in Cerro Alegre, we followed Monte Alegre once again to Paseo Yugoslavo where we could have taken our first ascensor (funicular) but the Ascensor El Peral was closed for repairs. Instead, we descended a long series of concrete stairs down to Plaza Sotomayor, the most important historical square in the city which features several impressive buildings as well as the Monumento a Los Héroes de Iquique that dates back to 1886.

Once we passed through the square, we entered the heart and soul of El Plan which was filled with businesspeople, small shops, shady looking characters, rundown buildings, and a darker shade of graffiti which somewhat matched the seedy feel of this place. We were told to hide all valuables and be aware of pick-pocketers. I had heard a few stories about petty theft so I heeded the warning from our hotel and kept my camera tucked hidden inside my jacket. We followed Serrano Bustamante to the Plaza Wheelwright seated below Paseo 21 de Mayo on the hills above.

I shot a few of these pictures along the way with my handy iPhone and included them to give you a feel for the area. The bright sunny colors of the street art in the more prosperous hills of Valparaiso seem to have disappeared and instead the art is slightly sinister feeling and dark. I found the art moody and reflective of some of the struggles of this area that has fallen a little off the economic wayside.

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Cerro Artillería, located in the southwestern hill of Valparaiso, received its name and prominence as a strategic military lookout area and base. Atop the hill is the Paseo 21 de Mayo, a square that has the best view of Valparaiso’s working port in the entire city and also is home to the fantastic Museo Naval y Maritimo for those who want to learn more about the city’s maritime past. I loved this museum and found it definitely worth a visit.

To reach the top of Cerro Artillería, you can either walk directly up the hill or else take an ascensor. We decided that It was time to take our first ride on an ascensor and quite honestly judging by the looks of it I was a little bit nervous. Built in 1892, the Ascensor Artillería is one of a handful of ancient funiculars transporting the people of Valparaiso for over one hundred years. Given Valparaiso’s steep terrain and multitude of hills (there are 42 cerros in all), these fascinating cars are part of the protected cultural heritage of Valparaiso and are considered historic monuments. They also save the legs and knees from all the hard walking.

We arrived swiftly at the top, and walked over to check out the lookout of the port below. Quite frankly, it was absolutely fascinating to see the scope and size of Valparaiso’s port. Containers were being loaded one on top of the other by bright blue cranes. The buzz and noise of the port could be heard all the way on top of the hill. I could only imagine what this must have looked like hundreds of years ago as it developed and prospered into one of South America’s most important ports.

After checking out the foggy views of the port, it was time to head back to our hotel in Cerro Alegre. Our fabulous staff at Casa Galos had given a recommended route to follow and we stuck with it since it had given us a lot of success doing our own self-guided walking tour. Instead of taking the ascensor back down, we followed an old-crumbling walkway down which was filled with art.

View of El Plan from above as we headed down. 

To reach the walkway, we walked a short distance north of the ascensor station and hung a left. The street was just as I had expected. Uneven, rundown and of course filled with art on every free inch.

By three o’clock we were back at our hotel for a short break before checking out the last neighborhood of our trip: Cerro Bellavista. My head was spinning from so much eye candy yet I was determined to do Valparaiso right. I would see and capture as much street art as possible.