After packing, finishing a last-minute badly timed work assignment and eating dinner, I decide to lie in bed for a couple of hours. It’s already almost 3 a.m., will I hear the alarm at 5:30 a.m.? Is it even worth sleeping?

There are Latino mysteries that still keep me awake at night—things I noticed in Brazil, Uruguay, Argentina and Chile that don’t make much sense to me.

I showed up with my passport and the email confirmation. I was half-expecting to be turned away—Chile is pretty bureaucratic, maybe I was missing a crucial document, some authorization, a piece of ID—but after a close passport inspection, the guard let me in.

I’m alone, I interact with people in Spanish and it looks like I know where I’m going, so most tourists assume I’m a local.

When I moved into the studio I’m renting in Santiago, I noticed several shopping carts parked by the elevator, in the lobby of the residential high-rise building. Every night, the shopping carts were gone for a few hours, and they would reappear the next morning.

I could do Valparaíso even better than last time, I thought. I would find a good map, brainstorm an efficient and scenic way to get from point A to point B and see everything I wanted to see.

You take off your clothes and lie there, half-naked, waiting.Your friends and plenty of women’s magazines told you it might hurt the first time.You’re not quite sure what to expect, but you’re ready.

Every time I go from one place to another, I feel like I’m hurling myself out into thin air. Taking a leap of faith out of whatever comfort zone you created into the unknown is scary but terribly addictive.

There are only eight kilometres between Valparaíso and Viña del Mar, seven metro stations from Puerto to Miramar, but the two cities are a world apart.

Despite the apparent lack of human logic behind city planning, life uphill is actually pretty normal. Around El Plan, the coastal strip … well, it’s another story.

Valparaíso is that place where you do exactly what you shouldn’t be doing in Brazil—getting lost in a maze of empty alleys and wandering aimlessly in colourful neighbourhoods built on impossibly steep hills.

From stray dogs to gated stairways, from bad restaurants to the logistics of staying uphill.

At first, everyone went according to plan. And then… well, not so much.

Valparaíso is backpacker central. Chile’s most colourful city is also a magnet for rich tourists, artists and pretty much anyone who lands in Santiago—it’s next door to the capital, only two hours by bus.

It took me a couple of days to realize that “my” neighbourhood, around Universidad de Chile, is basically Little Caracas. If the food isn’t from Venezuela, the vendors are.

Santiago packed most of the pubs and nightclubs in one neighbourhood, Barrio Bellavista.

“Let’s see… how much money do I need today?”I laughed at my own question. Considering the plans for the afternoon, whatever I have in my wallet never be enough.

“Tengo sed,” it said on the Cross.“I’m thirsty too, Jesus. I’ve just hiked to the top of Cerro San Cristóbal—and by the way, I have no idea how to go down. What’s your story, already?”

Concepción is worth a stop but you probably can’t appreciate it until you truly immerse yourself in campus life or academia.

“Did you have a good day?”“Well… No.”I can be bluntly honest with Feng, who knows exactly how fast travelling can go from “awesome” to “let’s get the hell out of here.”

The first thing I did in Concepción was to leave Concepción.

Initially, it was accidental.

I had a coffee, inexplicably served with a fork. Then I had another coffee, which also came with a fork—either it’s a Terminal Sur tradition, either the kiosco employees had worked the night shift and were as sleepy as I was.

“You’re such a good husband, always volunteering to pick up my prescriptions at the pharmacy!” a few Chilean women must have said.

I think I found out why.

Art nouveau, neo-Gothic, Haussman and neoclassical-Spanish buildings are falling apart, but they do it with style and the result is a fascinating barrio full of colours, churches, plazas and stunning murals.