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Chapter 54: Colombia with Columbia, Part 2

Headed to South America with 300 of my closest friends!

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This was originally going to be one big post, but 7,800 words later, I decided to divide it into two parts. We’ll pick up where we left off: the morning after a big Perro Negro night.

Tuesday, May 16th

There was a real musical chairs-esque reshuffling of sleeping arrangements last night amongst the Guatemala boys that led to Antonio, Tanmaye, Marcos, and Ben all in Ben and Maye’s room around 4 AM watching a very mid movie: The Witch, and five hours later, I woke up next to the human energizer bunny himself, Antonio Calderon.

Not that I’m complaining. Somehow, Toni, who had a room to himself, had two double beds, while Brody and I had two twin beds. This is also the third night in a row that I slept in a room that was booked under Toni’s name.

We were supposed to catch a 9 AM bus to Comuna 13 for a tour, but we also woke up at 9:02, so as you can guess, we missed that bus. Toni and I finally got up at 10, and he ubered over with Juanma and Majo while I scooped Brody and did the same. We got there as the main group was finishing their tour, and we caught the second half of a street performance on a basketball court at the base of Comuna 13.

After the main group headed back to the hotels, Hannah and Osbert joined Brody and me on our walk up the neighborhood. Comuna 13 used to be the most dangerous neighborhood in Medellin, but since the government cleaned up the area, it has become a major tourist attraction full of history, graffiti art, and beautiful views of the city.

We made our way to the top in ~20 minutes (shout out to the escalators), watched a hip-hop show, grabbed some coffee, then headed back down. We passed another 10 or so people from our group who also arrived late on the way down.

Hannah called a two-stop Uber to take her and Osbert to a restaurant in the city center and Brody and me back to El Poblado, but the location glitched on the driver’s app after stop 1, so Brody and I got another car.

We met up with Tanmaye and Ben (read: I tracked Tanmaye’s location and we stalked them) at a sushi bar in town, we chowed down on some fire sushi, then Brody and I took a fat two-hour nap.

Brody and I got up at five and ubered to town to hit the gym (Ben chose the mall over the gym, which says a lot about his priorities smh). We went to Ultra Gym in the middle of El Poblado, a super nice spot on the 20th floor of a skyscraper, where I worked out the last time I was here. To my entertainment, Brody happened to a be big “dance between sets” guy in the gym.

After the gym, we showered, I updated a newsletter, and we headed to Colosal, a restaurant 20 minutes away with a view of the city, for our 150-person dinner reservation courtesy of Ryan. I sat by Toni, Ben, Marcos, Juanma, Tanmaye, and Brody, and Juanma and I made tentative plans to get a crew together for a UGA football game in the fall.

We have all of these cultural trips to other countries, but one big piece of US culture that most of the LatAm crew hasn’t experienced is a college football Saturday in the south. A tailgate is really just an asado times 100.

A bunch of people from my cluster were sitting at the table across from me, and Maite, my favorite Brazilian whose dog, Olivia, has proven to be a valuable asset to my Hinge profile, accused me of not hanging with her enough and spending too much time with the boys.

It was a valid accusation, but also, have you met the boys? Come on, they’re sick. Still, I told her I would do the Guatape trip with her and company in the morning.

Our dinner came with two glasses of wine (which ended up being far more than two), and two beers (which could also be gamed by jumping tables to say hey to people, as I did with my star English student, JC), and the food was a lineup of fire tacos, fire entrees, and fire desserts.

After the main course, I recounted the previous night’s antics with Guillermo, and he informed me that at one point, he asked me three times “Me compras una cerveza?Will you buy me a beer?” to which I finally replied something along the lines of “I’m on my last brain cell, estoy borracho, use English.”

I blame Guillermo and Toni, who had both weaponized bottles of Aguardiente and poured them down my throat like they were filling a Ford F-250’s 40-gallon gas tank.

After dinner, I jumped in Tanmaye’s Uber back to the hotel, got ready for bed, and headed to Toni’s room to hang with the boys, where I joined a homoerotic Ben and Brody sandwich in the bed that I’d slept in the night before. Then I figured, “Might as well just sleep here again, it’s more comfortable than my bed.”

Toni unsuccessfully tried to reenact some TikTok video that Guille had sent, then I tucked him in, read him a bedtime story, and called it a night.

Don’t worry Cote, I’ve been taking care of your boy.

Wednesday, May 17th

Today, we’re headed to the town of Guatapé to scale the massive rock known as El Peñon.

Guatapé is a cute little town a couple of hours from Medellín, and this massive stone has made it quite the tourist attraction. I grabbed breakfast with my girl R Kelly, headed back upstairs to grab some water bottles and my Miller Lite tank top, and jumped on the next bus out. I landed a seat to myself across from Amanda, who made for a good bus buddy on our two-hour trip.

We left around 8 and arrived in Guatapé around 10, where we spent the next 45 minutes or so exploring the town. Guatapé is super pretty, with its brick and stone alleys covered by colorful umbrellas. Its streets are also lined with shops selling all sorts of knick-knacks and accessories, and in one particular store, I encountered the greatest piece of clothing of my life: A wolf poncho.

This poncho was an instant no-brainer purchase, and I wore it around for the rest of the morning. It was also a hit with the LatAm crew, who said I had now graduated from being “El Perrito,” or “the puppy,” to “El Lobo.”

Manu has unsuccessfully tried to get folks to call him “El Lobo” all year. The key is to simply buy a poncho with a wolf on it.

On my way back to the bus, I walked past Mr. West also purchasing a similar wolf poncho. It appears that great minds think alike.

I took the poncho off when we got back to the bus, because Colombia is really hot and not at all conducive to wearing an alpaca poncho in May, and we headed to the big-ass rock.

I hiked up said big-ass rock with Jen, Ben, Guillermo, Adam, and Bhavin, and after a sweaty 25 minutes, we reached the peak. The views from the top were insane, with hills, lakes, and miniature islands surrounding us in every direction.

Benny boy and I tried to grab ice cream at the top, but it was cash only, and we were card only.

We made our way back to the bottom, where we took the buses to a restaurant ~five minutes away. We were greeted with cold beers and bowls of rice, veggies, and chicken, and I posted up with Ray and Sophia (previous London travel companions).

After lunch, I made the rounds, showing off my wolf poncho (Caro, my concerned mother, said that I should take it off because it had to be hot. What she didn’t realize is that steez doesn’t care about humidity).

I then went downstairs to play beer pong (A US cultural import to remote Colombia) where Jack Sheridan and I promptly got our asses kicked by Ben and Jack Gorman (It was a Jack-centric game).

We hopped back on the bus back to Medellín, where I tried to write for a bit before succumbing to the bumpy roads and took a nap instead.

When I got back and showered, I realized that I got wrecked by the sun during the hike, and I had an insane tank top tan line.

Oh well.

We had rented out Medellín’s Botanical Garden that night, and the crew grabbed an 8 PM shuttle downtown for dinner. Downtown Medellín is a bit rough, but much like the mythical Camelot, the Botanical Gardens were a utopia in the eye of the storm.

The venue was beautiful, and I grabbed a seat with Laura and Manu, where I ended up being the token gringo in the middle of the LatAm crew. After dinner, the Colombians took the stage, welcoming all of us to their country, and then the DJ kicked the party off with a series of back-to-back-to-back bangers.

The Botanical Gardens party was 10/10, but it was going to wind down at 2, and some of Medellín’s premier nightlife spots stay open til 4 on Wednesdays. One of said spots is Perro Negro, the location of Monday night’s fiasco.

Emma and I grabbed an Uber back to El Poblado, and on the way back we were pulled over by the local police. Medellín has a real drug and prostitution problem right now, and the police have been using routine traffic stops to crack down on the issue.

Our driver got patted down, then Emma’s purse got searched, then I got pulled out of the car and interrogated. Thankfully, I speak functional Spanish, and much like flirting with a girl, the key to gracefully handling any cop situation is making him laugh.

He started going through the contents of my wallet, asking what was inside.

Cosas normales,” I said. “Tarjetas, dinero, etc.

He glanced at me and asked, “Drogas?”

I replied, “Drogas? No hoy.” (Not today.)

He started to chuckle (at this point it was so over).

He asked, “De dónde eres?”

“Nueva York.”

“Nueva York? Por qué tu tarjeta muestra Georgia?”

“Porque viví en Georgia antes de Nueva York.”

He then asked, “Y quien es?” glancing at Emma.

“Mi hermana, obviamente.”


“Jaja no, una compañera de clase.”

“Y a dondé vas?”

“La discoteca.”

“Por qué?”

“Por qué? Porque quiero bailar y tomar. Por qué otra cosa?”

At this point, he could tell that I was stupid, but not dangerous, and he wished us a good night. Here’s a photo of me chatting with the cop, peep my sunburn:

After the brief delay, Emma and I finally made it to Perro Negro around 1:45. I texted the boys that it was bumping, and we hit the bar in the back. Unfortunately, the boys were at some mid techno-club that was not-at-all bumping.

Oh well, we had a good time at Perro Negro, anyway.

Thursday, May 18th

Another day, another flight. This time, to Cartagena. Yesterday, Ben had tried, unsuccessfully, to get the boys to sign up for a 9 AM coffee farm tour today. Throwing on sleeves and long pants to tour a humid-ass coffee farm while hungover sounded pretty miserable, so I respectfully declined that offer. Instead, Brody and I packed up, checked out of our room, stored our bags, and headed back to town to hit the gym. Only one more day to get shredded before the beach party 😤

After a solid pump and gym shower, we strolled around town in search of some food. We ran into like three different groups of girls from our crew on the way to 37 Park, our restaurant of choice. I got an insane brunch: An egg skillet with chorizo and rice, a side of sausage, cheese, and tortillas, and French toast with fruit and vanilla ice cream.

God-tier post-workout grub.

After lunch, we headed back to the hotel to catch our shuttle to the airport. The shuttle itself was uneventful, but I got hosed when we reached the Avianca check-in counter. The Wonder Group reps handed out our tickets, and I noticed that mine said “Jack Raines.” In most circumstances, “Jack Raines” is a very normal thing to call me. I prefer that, even. But when I’m trying to board a plane, anything other than “John Raines” is problematic.

When we signed up for this trip, we listed our legal and preferred names on the website. Whoever booked these tickets got a few of the names backwards (my ticket from Bogotá to Medellín said John, btw), and I figured I was about to be screwed.

The Avianca employee said it wouldn’t be a problem, and I should just go to security. Having previously missed a flight from Edinburgh to Copenhagen because I put the wrong name, I knew that this was definitely going to be a problem, but I tried going through security anyway. I almosttt made it, but the worker showed her supervisor my ticket, and he ripped off the barcode stub and made me go to the ticket desk to get a name change.

I grabbed one of the Wonder guys, explained the situation, and he walked to the desk with me to try and clear up the situation. As it turns out, misery loves company, and another girl, Cherry, was in the same boat as me.

The Avianca ticket salesperson looked at our tickets and told us she couldn’t do anything, we’d have to buy another ticket. That’s actually pretty ridiculous because you can literally just print another ticket on the computer, but she wouldn’t do it.

So I had to buy another ticket (Wonder did pay for it, thank goodness), but the only flights available had a Bogotá layover, and I had to take an aisle seat in the back for both flights. Avianca is infamous for its minimal legroom and terrible service, and they certainly lived up to that reputation today!

I realized, too late, that if I had bought the new ticket without trying to go through security first, I could have gone through security with the new one and boarded the first flight with my original, because they weren’t checking passports at the gate, just scanning tickets. But I didn’t have my barcode anymore.

I tried to “dumb American” my way onto my original flight anyway, because it was leaving 15 minutes before my new one, but the Avianca reps politely told me to go kick rocks.

I then tagged Avianca in a very, very heated tweet, to which they replied that you can only change up to 3 letters on a ticket. That’s pretty funny, because “Jack” to “John” is exactly 3 letters, but no one helped me out. So thank you, Avianca, for solidifying your status as the least customer-friendly airline on the planet. Seriously, you make Spirit look like SpaceX.

Four hours, two flights, and a couple of Bogotá airport IPAs later, Cherry and I did make it to Cartagena, and we did secure an Uber to the hotel. I showered quickly and headed to the Old Town, the walled-in part of the city, to meet up with Brody and company at a bar. It was my roommate’s last night in town because he had to leave for a wedding the next afternoon, and we were going to send it.

I linked with Brody, Marcos, Guille, and Matt West at Alquimico, and we hit another spot across the street after. We headed back to the hotel around 1:45, big day on the water tomorrow, had to get our beauty sleep!

Friday, May 19th

Our shuttle to the pier was leaving at ~9:30, so I said adios to Brody (he didn’t want to go downstairs and catch mega FOMO) and headed to the restaurant for breakfast at 8:45. I grubbed with Manu, Laura, and Toni, then we lingered in the back to make sure we could all get on the same boat to the beach.

Our boat had several LatAm’s finest, but we had to spread out to even the weight distribution for the ride. I ended up in the back with Ben, Amanda, Jen, David, Bree and Caro (so we did get one LatAm rep), while the front was all Colombia/Argentina/Guatemala, plus Tanmaye.

The boat ride over was a vibe, but I was terrified of getting more fried after neglecting to use sunscreen on the hike on Wednesday. Thankfully Jen’s a real sweetheart and she did an ample job of covering my back ❤️

I hung out with Caro for the first part of the ride til she ditched us for the front of the boat, then Ben and I worked on our tans for a bit on the back.

When we pulled up to the beach an hour later, the scene was insane. Just beyond the sand was a massive dance floor with a DJ booth to the front, a bar to one side, couches to the right, and an elevated platform with more seats in the back. This whole setup sat under a two-story-tall beach cabin, which was supported by 20 ft high stilts. A brief self-guided (and somewhat off-limits) tour of the cabin upon arrival confirmed that this would be a 10/10 place to rent out with 40 friends.

While the water in Cartagena was murky, the water off the coast of our beach destination was crystal clear. The beach was lined with hammocks, and off to the left of the cabin was a large, covered patio and bar.

So yeah, sick setup.

I applied my 28th layer of sunscreen before grabbing a beer and hitting the water with Vince and company. About 45 minutes after we arrived, the DJ fired up the speakers, and a few heads started bobbing on the dance floor. An hour and a half later, after everyone had eaten lunch and consumed a few several more adult beverages, the place became an all-out rager.

Aguardiente bottles were being passed around like candy, and Toni (now with his girlfriend, Cote, in tow) was going nuts, spraying the crowd with water. NOT A BAD AFTERNOON.

Bienvenidos a mi blog, Cote (back right)

After three hours of grooving on the beach, we stumbled back to the buses to shuttle home. This was also when I realized that we weren’t on an island, just further down the mainland.

This particular bus ride took nearly two hours because of traffic, and my bus didn’t have a bathroom. This presented a bit of a problem for me, as I had to pee pretty bad about one hour in. But I couldn’t expect the bus driver to stop in the middle of the highway for one person. So I made the only logical decision: relieve myself out the bus window.

Relax, we were in the far right lane. No one was in the splash zone.

Once we got back to the hotel, Steph texted me and Ben to see if we wanted to join her and some girls for a dinner reservation. I said, “Sure, anything to ditch Tanmaye,” but I’m pretty sure Ben was KO’d for the night. A few minutes later, Agustin aka Bebé Normal showed up at my door asking if I wanted to go out. I informed him of the dinner invite, he happily took Ben’s spot, and we called an Uber after deleting the hotel beers.

We arrived at the restaurant in Old Town, and there was a bit of a wait for our table, so we hit the restaurant bar while we were waiting. I didn’t realize it until after the fact, but I had quite a buzz going from our day on the beach, and I kept the party rolling by hitting espresso martini after espresso martini (I was merely following Steph’s lead). I spent most of dinner chatting with Kristina and Agustin about God-knows-what, and after dinner Agustin and I tried to rally the troops to go out.

Dinner with Bebé

Morale was pretty low, but Steph, Emma, and I think Veronica headed back to Alquimico, the bar from the night before, with us. Agustin disappeared (and later sent me a selfie from bed, I guess the bebé got tired), and Steph and Veronica tried to get on the roof (No idea if they succeeded, the bouncer was a real asshole to us guys about it the night before) while Emma and I grabbed drinks.

We headed to the second floor, where like 15 people from Emma’s cluster were hanging out, and kicked it by the balcony for a bit before calling it a night around 2.

Saturday, May 20th

I was initially supposed to fly home on Sunday, but a few days ago, after talking to Tanmaye and Amanda in Medellín, I realized that 1) getting home at 9 PM on Sunday would be tragic and 2) I was probably going to be ready to bounce after the boat party.

Combine that with the fact that JetBlue gave me a $500 flight credit to switch from Sunday to Saturday and it was a no-brainer.

I got up around 9 and headed down for breakfast with Antonio and Cote, and after breakfast, we headed into the Old Town to explore a bit with Ben and Maye. Old Town Cartagena is so pretty during the day: it’s a quintessential colonial city: vibrant, colorful buildings separated by narrow alleys and cobblestone streets, all surrounded by a large stone wall.

We popped in and out of different stores, and I got a milkshake at a local gelato spot (Nina paid for it, finally getting even on our debt from when she rekt my drink night one in Bogotá). The boys had a silly little photoshoot, a mime tried to follow Toni until he realized that Toni was actually Colombian and not another dumb American, and we visited a super cool shop with homemade pottery, furniture, and jewelry.

We made one final stop in a clothing store where we ran into Jen and Caro, and Tanmaye and I said our goodbyes to everyone before heading back to the hotel to scoop our bags and hit the airport.

So yeah, that’s about it. Fun little trip to Colombia with Columbia, but it’s good to be back on my NYC couch for a few days. Stay tuned for what’s next 👀

- Jack

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