Well said.

Getting to Cuba was easily one of the worst travel experiences of my life.

Because of cost and schedule, we weren’t flying from Mexico City directly to Havana. Instead, we flew CDMX to Cancun on Volaris, where we were to pick up our luggage, check back in, go back through security, and fly Aeromar to Havana. We had about three hours between landing and departing, so plenty of time to make the transition, even with the added wrinkle of an international flight, and the extra complexity of that flight going to Cuba.

CDMX to Cancun went fine. For some reason I didn’t doublecheck our itinerary when we landed, and was convinced we were flying Aeromexico to Havana, not Aeromar. We landed in Terminal 2, and were told that international Aeromexico flights were out of Terminal 4. Given how much time we had, we waited 20 minutes for a free shuttle, rather than paying for a taxi between terminals.

When we got off at Terminal 4 to find our Aeromexico flight, well, it didn’t exist. That’s when I doublechecked and realized that we were actually flying Aeromar. Which was, you guessed it, in Terminal 2. At this point we weren’t going to wait for another shuttle, given how much time this mistake had already eaten. The cab fare for the five minute ride between two terminals: 1,000 pesos, or about $50 USD. Being stupid is expensive.

So we dash into the terminal, or as much dashing as two old people with four pieces of luggage can muster, and ask the greeters where to find Aeromar’s ticket counter. Now, you have to understand that there’s an ecosystem of people working in the airport who may or may not be there in an official capacity. And no one is wearing uniforms or tags that make it easy to distinguish whether they’re airport employees or the equivalent of racetrack touts. So all we know is that when we walk into the terminal, two seemingly random guys offer to help us. When we tell them we need the Aeromar counter, they shake their heads sadly and tell us that Aeromar is no more, that they are bankrupt.

Both the context and the intel itself make it very hard to wrap our heads around this fact-like information. I ask how to find out what our options are for getting to Cuba, and we’re pointed to an official Information Booth. That seems like a trustworthy way to find out exactly what the fuck is going on, so we head to the booth, and are picked up en route by a woman with a fanny pack who tells us she’s there to help us find our way around, once we get our intel from the Information experts. Nothing shady about that.

The Information Booth lady tells us that, in fact, Aeromar is dead, but that Viva Aerobus flies to Havana. Lady Fanny Pack asks what we were told, and then tells us she can get us to the Viva Aerobus counter. Which we’d passed on the way to the Information Booth, so it’s not like we don’t know how to find it.

When we get there, Lady Fanny Pack manifests someone to help us with booking on Viva Aerobus. This someone also doesn’t have any identifying insignia, and tries to help us standing in front of the Viva Aerobus counter, when behind the counter are three Viva Aerobus employees. The actual VA employees working at the VA counter, wearing VA uniforms, or Lady Fanny Pack’s helpful ghost? Not a tough call.
The nice VA lady we spoke to explained that yes, they had a flight leaving that evening for Havana. However, they didn’t have any seats left, as all the seats had been bought by a travel agency. She gave us the WhatsApp number for Octavio Mendoza and told us to reach out to him for tickets. Nothing shady about that.

She also shared that there was a charter airline that flew to Havana, and they were just a few doors down, with an actual counter and a real employee. We checked there, and yes, they flew to Havana, but one flight per day. If we used them we’d have to fly out the next day. Which meant finding accommodations in Cancun and taxiing back and forth. The fare itself wasn’t bad, but the overnight in Cancun sounded neither easy nor cheap. Time to find out about Octavio.Octavio told us he had seats on the evening flight out at 7:00. At this point, it was about 3:00, so we had plenty of time. He could round trip us for about $250 more than the charter, but we’d at least arrive the same day we’d planned, and we wouldn’t have to manage overnight in Cancun.

The only hitch? Who the fuck exactly is this Octavio guy? Some rando at the other end of a WhatsApp, promising that if we gave him money he’d get us round trip tickets to Havana. And how did he want this money? Cash, please.

That was a hard no. One of the things about visiting Cuba as an American is that there is zero access to the banking system. Credit and debit cards issued by a US institution simply don’t work in Cuba, meaning that you have to enter with as much cash as you need for your stay, because there is literally no way to get more. You can’t withdraw funds at a bank or ATM, and you can’t use a credit card for a purchase. So, while we actually had the cash for the tickets, we were no way going to part with it.
After explaining that we’d have to pay with a credit card, I also pointed out, as politely as possible, that this whole deal was shady as fuck, and that my confidence was very low that giving him my credit card would result in valid tickets to Havana. He directed me back to the Viva Aerobus counter to talk to Robert.

Robert, as it turned out, worked behind the counter, and seemed to be an actual Viva Aerobus employee. Or not. The David Lynch movie we appear to have entered was seriously messing with our ability to tell fact from fiction. Regardless, Robert was expecting us, as Octavio had told him we were on our way. Nothing shady about that.

I asked if we were going to pay him, and Robert said no, we’d pay Octavio, Octavio would release the tickets to VA, and Robert would print them out for us. How, I asked, were we supposed to pay Octavio? At which point, a guy with a credit card reader apparated next to us. Nothing shady about that.
Decision time: Cancun tonight, charter flight tomorrow, or… whatever this was. I figured I could always dispute the charge with Capital One if this didn’t work, and a night in Cancun sounded complicated. So… here we go.

I handed the apparition my credit card, and Robert explained that Octavio would have to issue the tickets and transmit them to Viva Aerobus for Robert to print, and that the whole process would take about ten minutes. Ten minutes between spending $800 and finding out whether we’d been scammed.
While we were waiting I got a message from Capital One asking whether the charge was valid. I decided to wait before replying.

As it turned out, it took less than ten minutes for Robert to hand us our tickets. I’m keeping Capital One in my pocket, though. We may have tickets, but we don’t have boarding passes. The process of getting boarding passes and providing entry documentation doesn’t start until 6:00, so we have a couple of hours to kill yet.

We grab a seat, and I open Viva Aerobus’s web site on my phone. Just a little status check, right? Turns out, my e-ticket just has a reference number from Octavio’s travel agency, not a Viva Aerobus record locater number, so I can’t look us up. OK, I can at least check flight status to make sure the flight exists, even if I can’t validate that we’re booked on it. VA’s web site reports that it has NO FLIGHTS from Cancun to Havana that day. Nothing shady about that.

So I go up the the VA ticket counter, not the kiosk where Robert and Octavio colluded, with our printed e-tickets and ask an agent to please, please, please confirm that they’re real. What I want is for her to look us up in their reservation system and confirm that we’re booked. Instead, she looks at the tickets and says, “Yes, they’re real” and hands them back. Clearly, everyone at the airport is in on the scam.
Now there’s nothing to do but wait until 6:00 and see if we can actually check in. At this point, I’m half of the mind that if this is a scam, Octavio has kind of earned our $800. I mean, the dude was working.
We queue up at 6:00, in a line that shows both our flight number and our destination. We’ll take any positive omens at this point. While we’re in line, some guy, again, no identifying ID, sells us our green Cuban tourist cards. I’d read that the cost was about $25. Mr. Man charged us $100 each. Whatever.
Then another guy asked if we had our Cuban entry questionnaire filled out. Why, no, we didn’t. You’ll surprised to hear that he had no identifying ID, but offered to help. Sure. Why not.

So he gave us the website address, and answered questions as we worked through the multiple page questionnaire, all in a rush, because it had to be done by the time we got to the ticket counter. Turns out, he really was there to help. For free, even. Nice.

We finally get to the head of the line, and the agent can’t find our reservation in her system. Here it comes. Then her supervisor figures out we booked through Octavio and shunts us to a second line. Where we meet a Canadian mother and daughter who had also booked Aeromar to Havana. Misery sure loves company.

When they’re done dealing with their real customers, they start on Octavio’s Orphans. Thankfully we get boarding passes, so it seems the last hurdle is over. It’s about 6:20 at this point, with a scheduled departure at 7:05, so we hustle to the international departure gates. And I finally let Capital One know that the charge was valid.

But was the drama over yet? No. No it was not.

At first, the departure screens don’t even show a Havana flight. After about 10 minutes it comes up on the board, showing an on time departure, but no gate assignment. The ticker at the bottom of the screen says that gates will be assigned no later than an hour before departure, but that’s a lie. It’s less than half an hour to departure, and still no gate assignment. All of this would fall under the category of normal airport fuckery, by the way, if it hadn’t been preceded by the telenovela of the previous 4+ hours.
Finally, the board updated at 6:45. Still showing on time for a 7:05 departure (sure…), but status updated to Go To Gate. Pretty hard to do, since there was still NO GATE assigned. The next five minutes were rough, but we finally got assigned a gate. In the terminal we were already in, no less!

So we run over to the gate, where a very casual crew is loitering in front of Volaris signs, not Viva Aerobus. After about ten more minutes, signs were updated to reflect the VA flight to Havana, and the crew eventually permitted boarding. Our On Time 7:05 flight finally took off at 8:15. Against all odds, we were on our way to Cuba.

With one more (at this point minor) bump in the road. More like a wee au revoir from whichever gods cooked up the day’s entertainment. Because sure, this happens on airplanes. Sudden condensation starts pouring out of the bulkhead for no apparent reason. But at this stage of the journey, you can forgive us for finding it ominous.