What is Valparaiso, Chile known for? Answer street art.

A dangerous port city or something a bit more? I went to Valpo for a week to give this city outside of Santiago a look. Viña Del Mar is just 30 minutes north with Concón sitting further north. Casa blanca is well known wine region is in the valley before you get to the water. Of all of these places Valpo has the worst rep. I love me a dirty suspect city so I booked a week at an old German house converted into a b&b.

The bus from Santiago is less than $20, runs every hour and is direct. Valparaiso is a city built on the side of a cliff. Truly each building is a feat of engineering, each supporting or threatening its neighbor. To truly appreciate this city here is what you should do. Bring cash and your walking shoes, it’s about to get hilly.

Book a place in Cerro Alegre. Known as the happy hill, it has the most beautiful street art in the world. As a self ordained global street art ambassador I was speechless at the art. Very single building, very corner, every staircase, ornate and beautifully drawn. I spent 5 of my 7 days exploring these hilly streets searching for art.

If you are a more lux traveler, stay in Viña Del Mar and take ubers or cabs over to Valparaiso. It feels like a Miami meets Northern Virginia vibe to me with high rises, massive malls, excellent restaurants and night life, all on a beautiful beach. Since Valpo is in a port the beaches aren’t swimmable. Concón is just a little farther north and were many locals in the area live. It is a little more affordable than Viña and a little nicer than Valpo plus it sits on a sand dune. Which takes me to my next recommendation…

Climb the sand dunes of Concón at sunset. My b&b host Paula drove me over to the sand dunes one day after I finished work. We grabbed a classic massive empanada and climb up and over the sand dunes to find the perfect place for sunset. The sky changes from yellow to pink to purple as the sand sits cooly beneath you.

Take a city walking tour. I was traveling Thanksgiving week so everyone on this tour was American, escaping the country during one of the brief vacation periods we have. My guide Felipe took us up and around all over the city including a subway ride, a bus ride, a funicular ride, tour of the fish markets, history about the street art, and through some crazy streets to find the best city views. Afterwards the family left, but Felipe and I grabbed a bottle of wine and hung in the backyard of my b&b. The other guy on the tour met up with us. We facetimed my family to wish them happy thanksgiving and grabbed sushi for dinner. I ended the day feeling very thankful.

Head to the forest, walk through the trees. I tried and tried to find a day winery trip for 1 person to the Casa Blanca region. Traveling alone and spontaneously booking trips has been overall successful but sometimes you hit a wall. Most tours require 2 people when booking. I guess I’d order wine at dinner and book a hike instead. The tour I took was with Andy, a local uni student. He didn’t speak English and knew a great hike through to a waterfall. We met at the plaza with 3 other people, all English speakers. One from California, said he spoke Spanish, like most Americans claim. The other two from Scotland and Singapore claimed no knowledge. Andy shepherded us on the bus and off we went.

I spent the day acting as translator as he explained the town outside the forest, park, lake, and other features. The Californian confirmed he can’t speak, he has like 3 phrases. I felt more confident in my understanding of the Chilean Spanish language because BOY is it different.

We met two older women while hiking. One was wearing a gorgeous skirt, I complimented her in Spanish. She tells me thank you and that she made it. Then proceeds to draw in the sand how I could make it myself. I listen patiently with no heart to tell her I thrift all my clothes. Speaking the language of an area allows you to have such an incredible experience, more than just seeing the place, you can feel it through the people.

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