A Gringa, Graffiti & a Gun: One Month in Valparaiso, Chile

When I quit my real estate job back in 2014, I did so with a dream of escaping the corporate grind. I was sick of monotonous routines, four-walled offices with no windows, and limited vacation time. Little did I know, three years later I’d actually have pulled it off. My office has expanded from a single small room to the entire world. I’m finally doing the digital nomad thing, and I couldn’t be happier.
As someone who works online, I’ve come to the conclusion that slow travel is the way to go. If you move around too much your productivity goes down, stress levels go up, and you don't give yourself a chance to enjoy the places you’re in. This is why I decided to drop anchor in Valparaiso, Chile for a month. I don’t think it’s a common choice, and many people have asked me why I chose this particular city. I don’t really have a good answer to that question; I just know I was ready to sit still for a while. Plus, Google mustered up some pretty persuasive images. Search “Valparaiso” and you’ll see what I mean- a sea of color by the ocean. 


Whether you’re planning to hang around for a while or just swinging through for a day or two as many travelers do- I’d like to share my favorite spots and what I learned. Valparaiso is a beautiful place to explore but hang around for the end and some tips on how to stay safe. For the first time in my life I had my life threatened, and there’s a few simple ways of avoiding the same situation, especially if you’re traveling solo. 

Where to Stay:

Personally, I’m a big fan of Airbnb. The place I settled on was a bit expensive, but since I was staying for a month, I wanted to have a room that I felt comfortable being in for long periods of time and could see myself working in. When I saw the photos for this room- I was sold. It lived up to my expectations completely and ended up feeling like home for a month. If you're interested in booking, you can find the Airbnb link here.

Sidenote: on the off chance that you've never signed up for Airbnb and want to give it a try, signing up using my personal link gives you $40 off your first booking! 


A bit about the house: it is run by a couple named Javier and Javiera (yup, I know), and there are a total of 4 bedrooms up for rent. You'll usually find at least one of them staying in the small 5th bedroom at the back of the house- so they’re around if you need them. There are two larger rooms with windows facing out to a beautiful view at the front of the house- mine was one of these. I won’t lie- it was cold. It’s coming up on winter in Chile and central heating is not a thing. I was typically sleeping in many layers of clothes under even more layers of blankets. The other two rooms run along the main hallway and have big windows, but these just face out to the hallway. Being on the interior, I imagine these rooms are a bit warmer. Also, the kitchen was totally equipped and was perfect for cooking in to save money. Food in Chile, like accommodation, is not the cheapest. In fact, I completely underestimated the cost of living in Chile. Don’t be like Lauren, research cost of living and average weather temperatures before you go somewhere.
If you want to splurge, I recommend this place 100%. Otherwise, there are many cheaper options on Airbnb. The other option I would recommend is joining the “Discover Chile” group on Facebook. If you’re looking for a place to stay, you can always post there and see if anyone is renting out a room. $600+/month for a room is not normal and you can absolutely do better.

Where to Eat:

I did my share of dining out while staying in Valparaiso, despite the hefty price tag. Here are the places I enjoyed the most:
Café Con Cuento
This spot is in Cerro Alegre, the touristy area where my Airbnb was located. They had good WiFi, fresh fruit juices, decent paninis and quesadillas. 

Valparaiso Chile Empanada.jpg

Foto Café
My most visited restaurant in Valpo. The fettucine alfredo is pretty delicious, and the pastries/cakes too! The staff are super kind and the WiFi was great.
Delicias Express
A delicious, hole-in-the-wall empanada joint on Urriola. They have a ton of combinations, you just tell them the corresponding number on the menu! You can't go wrong with chorizo and queso.
Café de Pintor
DELICIOUS set menus. The vegetable soup, beef roast, mashed potatoes, and mousse set was my favorite. Here you can also admire the amazing full wall mural made by a local named Mario. He's an old, adorable painter who actually chatted me up in the street one day and gave me a print of one of his drawings.

Cafe del Pintor Valparaiso Chile.jpg

Almacen Nacional
This was super close to the Airbnb and had a really nice ambiance. Unsurprisingly, I ordered pasta. They also had an amazing mixed berry fruit juice. 
…and for dessert:
Emporio La Rosa
It’s been listed as one of the best ice cream joints in the world. I can see why.

What to Do:

Valparaiso is best explored on foot, and there are plenty of walking tours available to accommodate:
GraFREEti Tour
 A standard tour for tips deal, this 2-hour tour departs from Plaza Anibal Pinto at 10:30 AM and 03:30 PM. You’ll hit both touristy and off-the-beaten path spots to see some of the best street art in the city. No reservations necessary, just show up!
Free City Tour or Tours for Tips:
 Same same, but different? A great way to get to know the city. The only difference I know of is that the tour guide from Tours for Tips look like Where’s Waldo. Again, tour is free but a tip of 5,000 or so pesos is expected.

Ride the funicular:
If nothing else, this is useful just to avoid walking up the killer hills of Valparaiso. It’s 100 pesos (.20 cents) and worth the experience in itself.
Take a bus to Viña del Mar or Concon:
When you’ve had enough of the street art and want a change of scenery, Viña is the next city over and it’s a cleaner, more commercialized place with restaurants, malls, clubs, etc. In Concon, there are some amazing sand dunes to explore that overlook the ocean. I’ll let photos do the talking on that one.

Pablo Neruda House
 Ok, so I spent a whole month in Valpo and didn’t actually visit this iconic tourist attraction. It’s the eclectic house-turned-museum of a famous Chilean poet, and apparently it’s pretty damn cool.
Santiago Wanderers Game
 A fan of football? There happens to be a stadium in Valpo, home to the Santiago Wanderers. You may need to team up with a local to help figure out how to get the tickets, though (my Airbnb host sorted that one out!). We paid 2,000 pesos for a ticket- the rough equivalent of $3.

santiago wanderers valparaiso chile football stadium.jpg

Visit the port
 Valparaiso is a thriving port city, and you can’t miss the giant ships and containers down by the water. Take a stroll down to the port and catch some of the action.


Traveling solo as a female comes with its fair share of challenges and of course, valid safety concerns. If you’re a gringa, you will stick out like a sore thumb in Chile. If you’re a gringa and you’re running around alone with a big backpack in an alley, you’re not only a sore thumb but now a target. This is precisely the scenario I found myself in:

It was 3:00 PM, broad daylight, and I was off to a café. My backpack was loaded up with laptop and camera- everything valuable that I own and need. I took a shortcut- a narrow, winding concrete pathway that gets me to the bottom of the hill faster. As I walked, I saw three teenagers coming towards me. A girl, holding a red Mother's Day balloon and talking on her phone, and two boys.

I got that inexplicable pit in my stomach when I saw them. I continued to walk, when one of them cut me off, revealing a gun at his side pointed directly at me. Was it real? I'll never know. I also don't know what he said nor what I was going to do- but in that moment I held on tight to my bag, cuz I'd be damned if that punk was going to take my stuff. That's when I heard a yell from above. Literally, a man hanging out a window had seen it all. The boy was trying to get my backpack off when the man screamed at them- and off they went, without hurting me, without taking any of my stuff.

I'd hoped nothing like this would ever happen, but I got lucky. And while I was scared then, the dominant feeling that followed was anger. I was angry that bad people can ruin wonderful places and experiences, and make me second-guess traveling alone as a female. I was angry that other people have the ability to make me wary of exploring new countries. But, I resolved not to let this mess with my head. I also learned an important lesson- I'm not invincible. So if you're in Valparaiso, there is a pathway located near the house pictured below. If you're traveling alone, please don't take it. Apparently it is known to be dangerous, and there are normal driving roads to get to the bottom of the hill, where you will be much safer. Parts of Valparaiso are very shady, so when possible, keep your valuables at home, find someone to walk with, and just be very, very alert. 

Headed to Valpo? Have any questions that I didn't cover? Leave them in the comments below!