When planning our trip to Santiago, Chile there was no question we would spend at least a few days in Valparaiso. Known as one of the best street art cities in South America, this UNESCO World Heritage city is an art lover’s paradise. Its 42 cerros (hills) rise steeply up from the sea resulting in a labyrinth of streets, alleyways, staircases and a handful of rattling ascensores (old-fashioned funiculars dating back to the late 1800’s), all making Valparaiso or simply “Valpo” as the locals call it, one of the most unusual cities I’ve ever visited.

Valparaiso’s grittiness, seasonal fog, run-down 19th century, colorful corrugated-iron mansions and stray dogs make a sharp juxtaposition to its world-class vibrant street art that seems to cover every single free wall, staircase and building in the city. It is literally a walking museum of art and for that reason, has an unexpected charm that is hard to shake. As a street art lover, I knew that I would be in paradise and Valparaiso did not disappoint.

We found an absolutely perfect place to stay in the lovely, quaint and locally-owned Casa Galos Hotel and Lofts located on Templeman street in Cerro Alegre. Built in 1885, the building was completely refurbished and beautifully restored in 2012 opening as one of Valparaiso’s premier boutique hotels.

The hotel is gorgeous inside with high ceilings, tons of light and windows and lots of common sitting areas to relax in. I especially enjoyed the rooftop terrace which affords fantastic views of the city and its many hills. I can only imagine how wonderful it would be on a sunny, hot day in January when the fog has lifted. The breakfast room was appointed beautifully as well and the staff was delightful.

The lovely breakfast room at Casa Galos

I love the wooden maiden. These used to be at the front of ships coming into port.

A sitting area

Casa Galos

Another sitting area

Rooftop sitting area

The view

After checking in to our hotel and unwinding a bit, it was time to take our first walk through the sinuous, steep hills of Valparaiso. I had heard so much about its amazing street art scene that I could hardly wait to see it all for myself.

I read that Valpo was the perfect place to get lost in however I didn’t want to miss out on any art. Thankfully we had excellent advice from the staff at our hotel who helped us plan out our route. Since we arrived in mid-afternoon, we would only have time to get a quick taste of all that Valpo has to offer. With a local map in hand, we plotted our course for the remainder of the day. We would be sticking to the neighborhood around our hotel, Cerro Alegre, which is one of best areas for street art. We would hit two other popular neighborhoods, Cerro Concepcion and Cerro Bellavista, the next day. 

As we left our hotel at the corner of Galos and Templeman street, we saw our first awe-inspiring colorful mural painted on the side of a neighboring hostel. The vibrant colors juxtaposed against the gray, foggy skies of Valparaiso made the art seem to pop off the walls. It was stunning, and just a tiny taste of what we were going to see the next few days.

Cerro Alegre is located a steep 15-20 minute walk up from El Plan the flat, congested and dirty commercial area next to the sea and the port. It is one of 42 Cerros (hills) that make up the city which reminded me in a strange way of part San Francisco part Havana given its amazing, spiderweb of alleyways, streets and hills meshed together with old run-down mansions all in various states of disrepair.  It is a city filled with irony and a surprising charm given that every open space imaginable is painted on with art and made to be beautiful amidst the grim. Even the somewhat seedy and urine-smelling streets around the port are filled with murals and art. Quite frankly, I have never seen anything like it before. 

Valparaiso was first inhabited by the native Changos, an ethnic group who lived off fishing and gathering in the area. In 1536, the Spanish conquistadors arrived and Valparaiso’s long and tenuous history as a sea port began. In the early days, Valpo was a required stopover for big ships crossing between the Atlantic and Pacific Oceans through the Strait of Magellan and Cape Horn in the south. Merchants, colonists and pirates from all over the world passed through Valparaiso’s port and it became one of the most important ports in all of South America.

The port hit is peak during the California Gold Rush (1848-1858) thanks to a spike in demand for Chilean wheat. The city grew upwards from the port, and wealthy merchants built luxurious mansions piled up high throughout the steep hills of Valparaiso. The 20th century lead to a swift decline given the opening of the Panama Canal and a massive earthquake in 1906 which destroyed a lot of the city. Slowly over time, Valpo recovered.

Even today, signs of disrepair remain and can be seen in the rundown mansions and mismatched cobblestone streets. Petty theft (especially on tourists) has been on the rise and even witnessed firsthand. Restaurants remain empty awaiting business during low season. However, the influx of street art has done wonders to spice up the city and bring in tourists from all over the world to see its amazing art. Today, this UNESCO World Heritage Site is one of Chile’s most popular tourist attractions which has helped clean up the city.

The contradiction between old and new, peeling paint and brilliant works of art, remain giving Valparaiso a fascinating contradictory twist and feel. Right across the street from our hotel, lies the Iglesia San Luis (a Catholic Church that was built by an English colony that lived in Cerro Alegre and completed in 1888). Then the next block over is a swath of art-deco newly refurbished boutique hotels and restaurants. Both is possible all within a single block.

As we headed over to the next street near our hotel, San Enrique, I was already in a picture-taking frenzy. There was so much art and it was indeed everywhere. I could not believe the diversity of the art as well. There were murals, stencils, graffiti and also art that incorporated plants that were growing out of the cracks in the buildings. Art was going up stairways, splattered across walls and rising up two to three story buildings. It was on doors, garages and garbage cans. It was everywhere and this was just the beginning of it.

After following the winding streets around our hotel, we arrived again at Templeman street where it literally ends for a long block. Alongside the rutted old remains of the cobbled street are two staircases of course painted in bright colors. Weeds grow out of the old street that obviously has become a hippie (and tourist) hangout.

It was also my first of many encounter with Valpo’s enormous stray dog population who vehemently guard their territory against passing cars (thankfully humans didn’t seem to bother them at all). Whenever a car would try to pass, a pack of dogs would jump in front of it and bark non-stop. It took courage for the driver to go. The large population of stray dogs also meant you had to constantly watch where you stepped so you wouldn’t have an unfortunate present on the bottom of your shoe. This happened to one unknowing tourist who stepped in dog doo, put his backpack down to clean off his shoe and lost his passport, computer and cellphone all in one moment’s mishap.

After exploring the funky streets of Templeman, it was time to walk around San Enrique and Lautaro Rosas streets in search of a place to dine later for dinner. Both streets were of course filled with street art and were quiet charming. It wasn’t going to be too hard to find a good place to eat as Cerro Alegre has become a foodie haven.

Heading down Urriola in search of more art and restaurants.

I loved this mural on this Italian place

It didn’t take long to find the perfect place for dinner that evening, La Cervicheria, an infusion-style fish restaurant with an outdoor terrace and fire pits. We were in for a real treat and had the entire place to ourselves.

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After a heavenly meal, it was time to go back and get some rest before our big day of walking in search of more street art. I was already feeling a bit overwhelmed. But I had to of course snap a few more photos on our short walk back to the hotel. I knew that the next day was going to be an extravaganza of photography! I could hardly wait!

Stay tuned….

My largest collection of amazing street art and guide on how to find it is coming next!

Want to go?

There are tons of great boutique hotels in Valparaiso. We loved the Casa Galos, located in the Cerro Alegre neighborhood at 893 Templeman. Tons of restaurants and everything you need is within walking distance from this hotel. Best of all, it is on a quiet street!