During my first visit to Chile I was curious to see Valparaíso, but I was pressed for time and decided to visit the Casablanca wine region instead (shockingly, I chose wine). When I returned to Chile the following year as part of a birthday trip with my good friend Karen, we decided to spend two days in Valparaíso. A port city that is also part of Chile’s second largest metropolitan area, Valparaíso played an important role in the country’s economic growth in the late 19th and early 20th centuries, but suffered a significant decline with the opening of the Panama Canal. In recent years it has reestablished itself as a college “town” with several large universities and liberal leanings. In addition, its many steep hills, colorful street art and unique funiculars give the city a distinct character and attract tourists from all over the world. Finally, it’s a quick trip from Santiago (less than a 90 minute drive), so Valparaíso can easily be done as a day trip if needed.

One note: when we visited Chile in January 2020, the country was going through a period of civil unrest, with demonstrations beginning in October 2019 after the metro fares were increased in Santiago, but also in response to growing inequality, the lack of a social safety net and government corruption. The largest protests that caused the most severe damage had already occurred well before our visit, but smaller demonstrations were still occurring regularly across Chile, although it seemed like these were centralized in specific areas of the cities that could be easily avoided. We never felt unsafe (in relation to the protests, at least), and it was fascinating to see the lingering effects of the unrest, and to talk with locals about their perspectives on the situation. The good news is that the government had already agreed in November 2019 to hold a referendum on rewriting the country’s constitution (fast forward to October 2020, and the referendum was passed).

This very detailed piece of street art from 2017 was created as a social commentary on Chile’s recent political situation (note the scary politician flying in from above with a U.S. flag-inspired parachute)

Getting to Valparaíso: An Unexpected Adventure

While we could have chosen to visit the city in a day through an organized tour (and many people do), we decided to enjoy a more relaxed pace. After two days in Santiago (check out my Santiago recommendations here), we rented a car and drove west to Valparaíso for another two days.

Renting a car in Chile was pretty easy, at least initially. After an initial hiccup at the Sixt rental office (spilt wine!), we received an extremely detailed tour of our VW Golf, including an explanation of the spare tire that would come in handy later (spoiler alert).

Oops, that orange ottoman wasn’t as big as I thought it was. RIP Maipo Valley Carmenere and Cabernet 🙁

The drive to Valparaíso was mostly easy. The roads in Chile are well-maintained and drivers are generally rule-abiding. We were making good time as we pulled into the city… until things got interesting. Cruising along the main highway in town, we suddenly noticed a truck full of young men shouting and gesturing dramatically at us. After a failed attempt at ignoring them, Karen rolled down her window to try shooing them away.

“Flat tire! You have a flat tire!” they yelled. “Follow us and we’ll help you!” Our scam radar immediately went off. It didn’t feel like we had a flat tire, but I also couldn’t see the tires from my vantage point in the driver’s seat. I eventually decided to follow the sketchy guys as they made a U-turn toward the hilly city (I would’ve pulled over immediately, but there was nowhere to park on the sea side of the highway). They tried to get us to continue following them into the narrow streets, but I stubbornly refused to leave the main road and parked illegally in front of a residential building.

“You can’t park there!” A guy from the truck came running up to us, again guiding us to follow them more deeply into the city. Ignoring him, I quickly jumped out of the car and confirmed that we indeed had a flat tire. UGH. Finally, I acquiesced and turned on the side street, where there was thankfully a small parking spot about twenty feet from the highway. The guy returned, attempting to get us to speak to him, but we continued to sit in the car as I pulled out our rental agreement to find the phone number for Sixt roadside assistance.

“What is your address?” the customer service agent asked me. UGH again. Of course I didn’t know. I jumped out of the car, holding my bag tight against my body and locking the doors behind me as I frantically looked for numbers on the nearby buildings and Karen attempted to fend off the guy still pestering us. “Thank you, we’ve got it handled,” we assured him as we locked ourselves back in the car. We had no idea if this dude was actually trying to scam us, but we weren’t getting good vibes and we weren’t going to risk it.

Sixt hadn’t been able to give us any kind of estimate on their timing, so we settled in for an uncertain wait on the side of the road. Approximately fifteen minutes later, we saw a police car drive up, and three muscular police officers got out. Oh shit, what was happening now? We could tell we weren’t in the safest part of town, and felt like sitting ducks as blond gringas in an obvious rental car with a flat tire.

Well, turns out the police officers were there to help us. A friendly man walking by spoke English and he hopped in to act as translator. Office workers in a building across the street had witnessed the earlier commotion as we were getting harassed by the supposed Good Samaritan and I was wildly searching for an address to provide to Sixt. The officers asked if we were okay and if we had been robbed. Thankfully, yes we were and no we had not. Apparently it was a not-uncommon scam in Valparaíso for robbers to seek out foreign drivers in rental cars, covertly slash one of the tires while the car was stopped at a red light, then pose as heroes trying to help in a time of crisis. When the clueless tourists got out of the car, the thieves would snatch whatever they could grab (phones, wallets, backpacks, etc.), then run off. Thankfully, we had been careful to stay close to the busy highway, and gave the men little opportunity to take anything from us or our car.

“This guy – he also mechanic,” one of the police officers then said, pointing to his partner. We quickly realized that they were offering to help us replace our flat tire. Forget Sixt roadside assistance. “You have a spare?” the cop/mechanic asked us. “Yes, yes!” And we knew exactly where it was.

Valparaiso police to the rescue!
While the cop/mechanic replaced our tire, another officer took my passport to complete a police report and proceeded to make fun of my picture (to be fair, it’s pretty terrible)

Within minutes, we had a working spare tire and the officers indicated that we should follow them to a tire repair shop. Wow, I really felt taken care of now. At the shop, one of the men walked in to explain our situation to the owner and negotiate a price to patch our flat. “3,000 pesos,” he told us when he came back (3,000 pesos was about $3). “No more. And keep an eye on your bags.” (Actually, there was a lot of gesturing and back and forth in broken English and Spanish, but I eventually understand that’s what he meant). And just like that, our newfound cop friends were gone.

I had read a lot about the Chile police force’s brutal treatment of residents during the country’s recent protests, and it was difficult to reconcile our experience with all that I had heard. It felt a bit weird to be two blond American women getting VIP treatment from the local police when I was critical of many of their other actions, but I of course wasn’t going to turn down their help. It was a strange reminder of the privilege that I have, not just in the U.S., but in much of the rest of the world, as a white person (although on the other hand, I had initially been targeted because I was obviously a tourist in a rental car… so being a blond woman in a foreign country doesn’t come without its own risks or challenges).

It was only after we were settled into our hotel and were rushing to meet the guide for our walking tour that I realized that I had never heard anything from Sixt roadside assistance. Had they even attempted to find us? I eventually called to let them know we were safe and no longer needed their help, and the agent didn’t seem too bothered. WTF?!

Where We Stayed in Valparaíso: Zero Hotel

After our unexpected adventure, we were eager to get out of the sketchier parts of Valparaíso and head up the hills to the safer tourist-friendly areas. The city isn’t exactly a mecca of luxury hotels, but we found the charming Zero Hotel, a large 1880s house-turned-boutique hotel that offered sweeping views of Valparaíso Bay and a beautiful private terrace and garden. With just nine rooms, the hotel felt intimate and unique, and was located in the Cerro Alegre neighborhood within walking distance to many attractions and restaurants.

Our double suite at Zero Hotel was also affordable (less than $200/night)
Close-up of the seating area
View of the bay from our room

With its steep, narrow, cobble-stoned streets, Valparaíso is not the most car-friendly city (not to mention the aspiring tire-slashing thieves!) We had planned to use our rental car only for the drive from Santiago, then to keep it safe in a garage for the rest of our two night stay (pre-arranged with Zero Hotel for a nominal additional fee). After our near-robbery experience, we were happy to say goodbye to the car and rely on our own two feet, Ubers and public transportation for the rest of our stay.

View of Zero Hotel from the colorfully-landscaped terrace

What We Did in Valparaíso

Private City Tour – We figured the best way to quickly get acclimated with Valparaíso was to schedule a walking tour for our first afternoon. This four hour tour that we booked through Airbnb was hosted by Fernanda, a local who had grown up in “Valpo” and started her own tourism company with a friend after graduating from university. It was a perfect introduction to the city – we walked through many different neighborhoods, rode some of the funiculars, saw the city square that had been the site of the recent protests, and took a bus down to the water. Fernanda also pointed out some of the most notable of the many street art pieces throughout the city, explaining the meaning behind the more political of the works. While our tire fiasco had delayed us a couple hours in meeting Fernanda, she was very flexible with pushing back the timing (it helped that it was a private tour).

Overlooking the port of Valparaíso from Paseo 21 de Mayo (despite being overshadowed by the Panama Canal, the port still received a decent amount of traffic)
Example of the colorful buildings and street art that can be found throughout the city
One of the funiculars that we rode
A lot of the city’s stairways were painted with bright colors and messages
One of the many dogs living in the city. Fernanda explained that the residents of the community had essentially adopted these dogs, communally building them dog houses and providing them with food and water. They certainly looked happy and well-cared-for
Another creative stairwell
View of Plaza de la Victoria, where the protests in the city originated. Every time we walked nearby this square, we’d get whiffs of pepper spray that the police continued to use to deter demonstrators, so we didn’t spend a lot of time here, but it did seem to have some cute sidewalk cafes

Dinner at Fauna Restaurant – For our first night in Valparaíso, we dined on the terrace of Fauna (also a boutique hotel) in Cerro Alegre. The food and cocktails were terrific, but the real star was the view. We made sure to time our dinner with sunset.

Golden hour view from Fauna

Stair-Running Workout – I realize that running stairs may not appeal to everyone, in which case just walking the many stairways throughout Valparaíso is still an excellent workout! I’m not sure I’d recommend the city to people with mobility issues, as all the hills, stairs and cobblestone streets make for quite an urban hike, even if you’re not intending to get any exercise. Since Zero Hotel didn’t have a gym, Karen and I decided to design our own workout by jogging through the hilly city and running up and down every set of stairs we could find. It was HARD. One nice thing was that because Valparaíso is on the coast, the fog rolls in over the evening and then burns off by the afternoon (at least in the summer). The cool mornings were refreshing after the unrelenting heat in Santiago.

Karen, running up some rainbow-colored stairs
I liked this one: “Without fear”
One of the aforementioned “communal” dogs looking comfy in its well-built house

Casa Museo La Sebastiana – The poet/politician Pablo Neruda is one of Chile’s most famous historical figures, and three of his homes have been turned into museums. I had visited La Chascona, his home in Santiago, and had been impressed by its whimsical, offbeat design, eclectic art, and unique furniture and household items collected during his travels around the world. La Sebastiana was Neruda’s home in Valparaíso; the third museum is his home in Isla Negra, where Neruda died in 1973. It’s a quick self-guided tour through the museum; audio guides are provided and we completed the circuit in less than an hour. We also enjoyed walking around the surrounding neighborhood and its many viewpoints.

Unfortunately, it’s not permitted to take pictures inside the house, but you can get a rough idea of Neruda’s eclectic style from the exterior

Drinks at The Brighton Hotel – Another hotel/restaurant, The Brighton is in Cerro Concepción, neighboring Cerro Alegre. We got a table on the terrace overlooking Plaza de la Victoria, wondering if we’d be able to watch any protest action; we didn’t see anything happening, but the Negroni was perfectly-crafted.

Like many of the hotels in Valparaíso, The Brighton is a converted historic home
This view of the fog rolling in over the hills reminded me so much of San Francisco

Getting Back to Santiago

We had to drive through the sketchy area of town once more to get back to Santiago (there is only one route), and I had no qualms about speeding through the streets as quickly as possible while Karen scanned our surroundings with laser focus. Just to be safe, we also locked all of our valuables in the trunk and only kept our phones with us. Fortunately, the drive back was uneventful, and the Sixt office didn’t charge us anything extra for the damaged tire (it seemed to hold up just fine with the patch), especially after I complained about the roadside assistance team’s lack of follow-through. We had a good story to tell upon our return to New York, and it thankfully didn’t have a bad ending.

While our trip to Valparaíso started out with a scare and we faced a (low) risk of civil unrest due to the political climate, I’m happy to report that we felt completely safe during the rest of our stay. I would not discourage anyone from visiting, but I would be very careful if you choose to drive yourself in a car that is obviously a rental, and I would stick to the touristic areas of the city, unless you’re with a local or a guide. A small group tour may be a better way to visit for those that are worried about safety.