My Favorite Underrated Cities: Part 1-a, Santiago

Kenneth Tsai
10 min readJun 30, 2024

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The cities that I love even though everyone told me not to stay for long

2024/03/15 — 2024/03/20.

I am starting a series depicting some of my favorite places during my trip. Cities which are commonly considered quite “boring”. At the time of writing, Santiago, Bogota, and Sao Paulo were the ones that came to the top of my head. Many can probably deduce the common denominator by now: they are all mega metropolitan cities with few notable tourist sites. As much as I appreciate the beauty of nature and small towns, I’m a city boy by heart at the end of the day. More importantly, I feel that big “living” or “working” cities are more of a realistic representation of the people and the culture.

Starting with Santiago, Chile.

The bus from Mendoza and the Chilean customs affairs

I arrived in Santiago, Chile on an 8-hour bus from Mendoza, Argentina, crossing the border. I missed the initial bus I had paid for because I remembered the time wrong (I wrote about it here). The solution — I just paid another 50 dollars for the next bus departing within 20 minutes. Painful but easy.

The ride from Mendoza to Santiago illustrated

The bus ride from Mendoza to Santiago is famously very enjoyable. The bus goes through the winding yet stunning Andes, crossing the border control INSIDE the Andes. The bus experience itself is also very comfortable: semi-cama (half-bed) type seats, and not many full on each bus because the route departs as frequently as every hour. You have so much space and magnificent views presented so close to you that it feels almost as if you were the only person on that journey. I put on a downloaded Podcast and just looked outside the window the whole time.

The roads are winding, and once you get to the lower part of the mountain you can clearly see all the other buses and cars on the same route

There was a small episode at the Chilean border control. Our bus got to the border control, and we were asked to take our carry-on bag to walk into the Customs (Aduana) building and wait in line. We were the only group of people there, and they were sooooo slow to process.

This was the whole queue and only two people were processing us

Finally, it got to my place, which was almost at the end of the queue. The officers looked at my passport and said, I need to check if you need a visa, so they went on to ask somebody on the phone. Traveling as much as I have, I knew what was happening already. So I hold a Taiwanese passport, which says “TAIWAN” on the cover, yet on the personal data page it says “the Republic of China”, so they assumed that my passport was from Mainland China. I told them in Spanish — no, this is a Taiwanese passport; the real Chinese passport is red. They were so caught up in their own confusion that they started going through my visa pages and flipping through the pages to see if I had any other visas that would qualify as a “visa waiver”. [By the way, I don’t need a visa to begin with.]

Meanwhile, I stood there fully thinking this was so stupid, so I tried to search on my phone for their official External Affairs Department’s website for any official visa-free list I could show. Guess what, I couldn’t find it. I got irritated because even Colombia has it very clearly and publically available, and their visa application website would constantly break down. After a few seconds, the officer walked out of his booth and said to me, “I can’t let you in because you need a visa.” I obviously was not about to give up, so I explained that I even entered Chile less than 2 weeks before, showing them the entry and exit stamps. And that’s what it took for them to understand. During this whole back and forth, I was the last person from the bus to still be stuck at the counter. One of the drivers waited next to me and I was, the last person to get back on the bus.

I stuffed myself with more Takis to calm my nerves. The journey continued.

The blue Takis I got in Argentina because I thought it would be cheaper, but Chile was one of the cheapest countries to get this iconic Mexican corn chip brand

Arriving in Santiago

The bus terminal

I arrived in Santiago at around 7 pm, about 9 hours after our departure. I had no data, and I had assumed that there would be wifi in the bus terminal. I was wrong. I ended up finding a kiosk in the terminal to buy a local SIM card. The girl was friendly and helpful, but I didn’t understand half of what she was saying and had to ask her to repeat it many times. It was my first encounter with the infamously difficult Chilean Spanish.

The place I stayed at for the first 2 nights

Chile is a relatively expensive country. I normally budgeted around 25–30 USD a night for accommodation on average, but even many of the hostel prices were close to that. I was told to stay in Providencia or Las Condes (Thank you Edu), which are safe places to be walking around even at night, but are also richer and hence more expensive.

As a result, I decided to stay in a hostel for the first 2 nights and see how it went. The place was very cozy, and it came with a free breakfast that the owners would make for their guests every morning. It’s a rather quiet, guesthouse-feel kind of place, so normally the common room would have maybe 1 or 2 people minding their own business or watching TV. I made a few friends during breakfast just by asking random questions. The guests there were extremely friendly and willing to take the time to chat. It was a good mix of foreigners and Chileans who came from other parts of the country.

The breakfast looked like this every day — the pot is where they put the scrambled eggs in

Some of the most friendly people

Being probably the “most developed” and expensive country in South America, I had expected the people to correspondingly be a little less personal with day-to-day interactions. I was pleasantly surprised to learn that the people there are genuinely warm. I think due to the cozy atmosphere of the hostel, I spoke with almost everyone I came across, and everyone was so sweet and willing to get to know you. I ended up chatting for hours and hours on end with my roommate Felipe, and we even spent the whole morning exploring the city together right before he caught his flight back to Temuco.

Picnic to kill time before he left
This was the view from where we sat

I kind of felt proud that I was able to speak enough Spanish to fully experience all the kindness and warmth people shared. I think he probably slowed down his talking speed for me and cut out all the Chilean slang so I could understand. I spoke with another guy who was also from Temuco at the hostel, but I could barely make out what he was trying. It was a strange phenomenon that was very particular to Chile.

The food that cost almost 10 USD but tasted honestly really mid

From the hostel, I also made plans with a Brazilian regional influencer who’s very gay and good-looking, but his content is funnier than it is thirst-trap-focused. His English wasn’t great and my Portuguese was barely existent, but we got lunch and went to Sky Costanera for an afternoon. The food was not great but edible. I simply accepted it because I had searched up on Chilean cuisine, and the only things I could find were sandwiches, hot dogs (completos) with guacamole, and some expensive seafood (like 25 USD) places recommended by my doctor friend. In hindsight, it was still affordable, but I was approaching the end of my trip, and I had gotten used to eating for 8–10 dollars a meal by then.

Us walking towards the mall which was about 1.5 km away from the hostel

We got to Cenco Costanera, the mall where the observatory is located. The entrance to the top floor was 18 dollars per person. I don’t regret the experience of going up, but I would not go up again. It’s much like the observatory of most cities’ tallest buildings, except with the view of the Andes.

The mall Costanera

The mall was probably considered one of the nicer ones in LATAM, but if you compare it to Hong Kong, it would be one of those Kwun Tong or Mong Kok malls — still nice, but it’s an affordable mall (rather than luxurious) filled with people.

The top, half outdoor floor on the observatory
Me being characteristically awkward with the posing

The panoramic view of Santiago was quite nice though. On the one side, there is a river by the famous hill, Cerro San Cristobal, also my favorite place in this city.

Cerro San Cristobal

The other side had the tall triplet buildings and the Andes at the horizon. I went in March and the weather was warm and very comfortable, but I saw some Instagram reels showing the city in Fall or Winter, and the view turns into another magical shade of color and snow would cover the peak of the mountain range. It might not seem like it from the picture, but visible from within the city of Santiago on a clear day, the peak of Cerro El Plomo has an elevation level of 5,434 m.

The Andes and the Financial district of the city, which gave me a strange sense of comfort and familiarity

Staying on the topic of talking to strangers, I even randomly met an American who had lived in Taiwan before and spoke fluent Mandarin. I borrowed his charger for a morning while he went to get a message with his girlfriend.

Cerro San Cristobal — best Santiago memory

My favorite piece of memory in Santiago was from Cerro San Cristobal, a famous hill overlooking the city, where one can take a tram (like the Peak Tram in Hong Kong) up to the observatory area. I chose to go around 6:30 pm as the sun sets around 8 pm at that time of the year.

The tram ride

There are a few restaurants up there. Very quickly I noticed that almost everyone had a cup of weird, sugary dessert, almost reminding me of the bean/syrup/grass jelly type traditional desserts we have back in Taiwan. I looked around and figured out they were called Mote con Huesillo, and it was only 1.5 USD. I immediately got myself a cup. It’s made of peach, sugar, and the large grain type of white corn called “Mote”. It was very refreshing and tasty.

The view from where I sat and ate the dessert

There is the option of taking the cable car down to ground level again, but I chose to walk down the hill as I heard the views were incredible. And they were. The walk was along a descending path, which was an extremely scenic path with a view of the city. I was so happy as I walked down and enjoyed music from my AirPods. Yes — I felt safe enough in this city that I almost always took them with me outside.

Starting the descent

Following the road, I saw a sign that said “picnic area”, and there I saw a small group of people smoking, drinking, and snacking, with music playing out from the speaker. As most people choose to go down the hill with the cable car, I was one of the few visitors to that area. We greeted each other, and I asked to sit with them. The 3 kind Venezuelans welcomed me and offered me everything they had prepared. We hung out, smoked, and drank as the sun set into the beautiful backdrop of Santiago.

The sunset — this was about 8pm
A little bit later
And then the lights darkened

At one point honestly, I just thought I would stick with them for as long as they stayed. They all had to work the next day, and I didn’t know how safe the way down was (it was very safe and very well-lit).

The four of us walking down at like 10 pm blasting out old school (Don Omar et al) reggaeton and them fully singing to all the lyrics. I loved it.

We all went to one of their places and had another drink before parting our separate ways on an Uber. I had an absolute blast, and I was so incredibly grateful for them and for the effort I had put into learning Spanish.

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Kenneth Tsai

Taiwanese 🇹🇼 living in Hong Kong. Madrid, Spain 🇪🇸 for exchange in 2022. Spent 4+ months solo traveling LATAM. I blog to record all these experiences.