Tailors and Terrors in Bogota

Old Bogota.

A quote attributed to Terry Pratchett, "Why do you go away? So that you can come back. So that you can see the place you came from with new eyes and extra colors. And the people there see you differently, too. Coming back to where you started is not the same as never leaving."

At a point somewhere between being held up in Egypt and suffering through the worst sickness of my life in England, I decided I was just getting started with this whole traveling thing. I liked seeing the world differently ala Terry Pratchett. It was time to embark on a new adventure, one I'm calling it Season 2 of my travel monologues.

It started when a family friend—retirement-bound and in search of paradise—asked me about Curaçao. I had fallen head over heels for the place after Googling “gay-friendly tropical island” one-night, post-twelve-hour workday meltdown when the days were short and I was driving home in pitch blackness, during what felt like the world's longest day/week/month at work just like the *Friends* theme song says. My ex and I had visited the island twice—once out of curiosity after the Google search and a second time in a last-ditch, inevitably doomed effort to save our relationship.

Fast forward to 2018, and the same family friend asks if I’d join him on a trip back to Curaçao to scope out real estate. I agree, using it as an excuse to explore more of South America. The plan? Fly to Bogota for a brief stopover, head to Curaçao for ten days of real estate hunting, then part ways as I continue on to Peru to finally see Machu Picchu. The historian/archaeologist in me was gaga with this idea.

Arepas and beer - my main sustenance in Colombia.

The journey begins with a penny-pinching shuttle ride from California’s Central Coast to LAX—a frugal decision that will come back to haunt me. We breeze through check-in at LAX, indulge in the international terminal's Star Alliance lounge, and board our Avianca flight to Bogota on a brand new 787 containing questionable pop-out tv screens without a hitch. So far, so good.

Bogotá, with its modern skyscrapers juxtaposed against colonial churches and a history stained by conflict and resilience, quickly takes center stage. After a red-eye flight, we land in the early morning, groggy and grumpy. I call an Uber to take us to the Hilton for early check-in, and the app directs us to a pickup point that feels less like a designated spot and more like the opening scene of a crime thriller. As we drag our suitcases over curbs, potholes, and through dirt, I can't help but think, "This feels about as safe as two gringos flaunting their luggage in a country once ruled by drug cartels." But, Hey, what's life without a little risk?" I try to tell myself in an attempt to lower my anxiety level.

Bogota's traffic.

Our driver, a fast-talking local, gestures for one of us to sit in the front seat and insists we handle his car doors with care. I'm not entirely sure we’re understanding him correctly, but once we’re on the road, stuck in Bogotá’s infamous traffic, the only thing I can focus on is whether this is the smartest idea I've ever had.

Spending time with someone in my parent's age bracket is a unique experience. While I’m typically an early-to-bed-but-still-not-a-morning-person kind of guy, he’s in bed by sundown and up before dawn—a nuanced yet stark contrast in lifestyles.

We spend our first day in South America walking around Bogota, when the family friend was repeatedly stopped by police and told to hide is DSLR hanging over his shoulder because of the risk of theft.

I wonder what crime this bird committed.

The city of Bogotá, founded in 1538 by Spanish conquistador Gonzalo Jiménez de Quesada, has a history as rich and textured as the traditional ponchos sold by street vendors. Nestled high in the Andes at 8,660 feet, Bogotá has been a center of power and culture since the days when it was the capital of the indigenous Muisca Confederation, long before the Spanish ever set foot on the continent.

Fast forward a few centuries, and I find myself stuck in Bogotá traffic, a city once more associated with drug cartels and crime than with its colonial charm and architectural beauty.

Our first day in the city leads us through La Candelaria, Bogotá’s old town, where the echoes of Spanish colonization are preserved in its cobblestone streets and beautifully aged buildings. Here, we wander through narrow alleys that have witnessed everything from the revolutionary fervor of Simón Bolívar—who plotted Colombia's independence from Spain right in this neighborhood—to the artistic revolutions of graffiti artists who now claim these walls as their canvases.

We visit one of the highest rated museums on Earth, the Museo del Oro, a place that houses over 55,000 pieces of pre-Colombian gold, a testament to the advanced metallurgical skills of Colombia's indigenous peoples long before the Spanish arrived with their own ideas of wealth and conquest. The museum is a stark reminder that while we come and go, drawn by our own curiosities and desires, the land we stand on has stories far older and more profound than our own fleeting moments.

A taste of what's housed at El Museo de Oro in Bogota.

But history is not all that Bogotá offers. After exhausting all tourist options and feeling like I'm not interesting enough for the family friend, I blurt out, “Let’s go to a tailor and buy a suit,” more out of desperation than inspiration after hearing from a former grad school classmate about his suit shopping spree in the city.

We end up at Vestido Guillermo Ortiz, a tailor shop that feels lifted from another era. It’s a far cry from the upscale boutiques of New York or London, but in the back streets of Bogotá’s industrial zones, there’s something timeless about getting a custom suit. The industrial-feeling area in which the shop is located adds to the experience.

Inside, no one speaks English, so we resort to a mix of hand signals, nods, and hopeful smiles. I select a Peruvian wool suit in charcoal gray, a white dress shirt, and a tie, feeling like I’m starring in a Bizarro Universe version of "Pretty Woman" where Julia Robert's character is allowed to shop, and also is a man. Guillermo Ortiz himself takes my measurements, calling out numbers to his assistant while I stand there, mildly uncomfortable but committed to the experience.

THE Guillermo Ortiz. He's probably seen it all given his ability to craft a suit for someone who doesn't speak Spanish.

With the suit ordered and a ten-day turnaround agreed upon, we step outside, where our Uber awaits. Or at least, that's what I thought. What actually pulls up is a tiny, unfamiliar car. It's dark and cold outside by this point, and it takes our eyes a few minutes to adjust to the car's interior, at which point we realize we're being driven by a teenager dressed as a vampire. Oh, right—it’s Halloween. The driver, clearly in the spirit of things, decides to take us on a shortcut through mountain roads, bypassing traffic in a way that feels more like a rollercoaster ride than a commute. I reach for my seatbelt, only to find there’s nothing to buckle into. "I’m going to die in Colombia, driven by a vampire," I think, as we whip around curves on an unlit mountain road at breakneck speed. It’s one of those surreal moments that travel so generously offers, where the past and present collide in a way that makes you question reality.

"Can this be real?" I ask myself.

By some miracle, we make it back to the Hilton in one piece, where we’re greeted by a security team and a golden retriever that inspects the car for explosives—a routine part of life in Bogota, apparently. It's always difficult to avoid bending down and petting a dog that's doing serious work rather than simply acting like a very good boy. Completely fried, I head straight to the hotel bar, order a locally brewed beer, and try to decompress while my family friend retreats to his room. This is also where I have my first taste of arepas, which I’m still trying to define, given the loose interpretation of what qualifies as an arepa in Colombia and Venezuela.

Beer by Bogota Brewing Company in the Hilton's bar - badly needed after your Uber driver is a vampire.

The next day, we make the trek up Monserrate, the mountain that looms over Bogotá that is a pilgrimage site, a tourist attraction, and a testament to the city’s complex spiritual landscape. Rising to 10,341 feet, the mountain has been a sacred site for centuries, initially revered by the indigenous Muisca people and later by Catholic pilgrims drawn to the 17th-century shrine dedicated to El Señor Caído (The Fallen Lord). The journey up, whether by funicular, cable car, or on foot, (we chose funicular due to the serious lack of oxygen) is a rite of passage for locals and visitors alike, offering breathtaking views that remind you of Bogotá’s sprawling expanse. From the summit, the city below appears almost serene, a far cry from the bustling chaos of the streets—a place where history, spirituality, and nature converge in a panoramic experience.

I walk around and take in the incredible vista, then sit down for a salad in the mountain top restaurant where I am surprised to hear a cover of Michael Jackson's thriller in a jazzy basso nova style while I enjoy a Cesar salad. The best things are those that you find in unexpected places.

Thrilled to have made it to Monserratte's altitude alive.

On the way back to the Hilton, I spill an entire bottle of water that I'd been carrying around in my backpack in an attempt to stay healthy and hydrated in my lap—because why not? —and end up soaking the back seat of a black SUV that the hotel had sent out to pick us up.

Our last stop before Curaçao is a Juan Valdez coffee shop—a name that brings back memories of semi-racist 1970s and '80s coffee commercials. I can’t help but think of how Bogotá is a place of contradictions—where beauty and danger walk hand in hand, where history meets the present in unexpected ways, and where even a simple trip to buy a suit can turn into a brush with the absurd.

As I sip my first Colombian coffee, the words of Terry Pratchett echo in my mind: "Why do you go away? So that you can come back." Perhaps that’s true, but right now, all I want is to stay a little longer in this city that feels like it’s straight out of a magical realist novel—part history, part fantasy, and entirely unforgettable.

We brave the traffic one last time while driving to the airport. Once through security, we head to the Avianca lounge while we wait for our flight. Once on board, I noticed metal markers with pilot and flight attendant names on each seat. It seems like a strange way to memorialize a person, particularly if they are no longer on this Earth.

To make things feel even weirder, the toilet on Avianca's Airbus toilet decides to take revenge on me. While using the restroom mid-flight, the pressurized toilet shoots water directly into my eye. Panic sets in as I envision a scenario involving bacteria and eye infections. I don't want to spend any portion of this once-in-a-lifetime trip sick. I try to rinse it out with my own tears, because I don't trust airplane sink water

The airplane with the explosive toilet.

All I want now is to reach our tropical island destination, find a beach bar, and chill.

If there's one thing travel has taught me, it's that multiple things can be true at the same time. A city can be historic and modern, someone can be a good person who makes questionable decisions, and I can be on my way to paradise with toilet water in my eye.