This post has been two and a half years in the making, and was underwritten by National Lampoons. I wanted to give the memories time to rest and be thoroughly evaluated before writing up the unbelievable list of events. This story contains a cavalcade of mishaps and horrible events that seem like they are ripped from the highlights of the latest comedy movie. I’m not the best writer and so this may read horribly and be too wordy. I assure you, all of these events happened – some of them I even have paperwork to prove.

About the time travel restrictions were letting up in early 2021 my girlfriend, Jen, and I decided to take an extravagant (for us) trip to Puerto Rico. Neither of us have passports and so it was the best island choice we could do on short notice before travel prices started rising again.

In March 2021 we jumped on a great price for round trip flights from the mainland to PR. The trip wouldn’t be until June so there was plenty of time to buy appropriate clothing for the climate and to plan what we wanted to do while there. Our flight was scheduled to come into San Juan and then have a rental car for the week.

Our stay was on the west side of the island in Cabo Rojo. The area is much less touristy and we planned to enjoy the beach and sun while visiting some spots like the bio luminescent pools.

Purchasing of breezy attire and sunblock was completed. Our bags were packed and well under weight. I was nervous about flying for so long at one time. STL to Dallas wasn’t a big deal but the flight from Dallas to San Juan was going to be a long one for someone six feet tall and not skinny. Still, this was a big adventure and I couldn’t wait to experience a part of the US that I had never before considered a destination.

The adventure begins…

We arrived at the airport terminal at about 1030. Our flight was scheduled to leave at 1pm and so we had plenty of time to check our bags and lounge around excited for our trip of relaxation and escape from the daily trappings of Midwest life. Soon we’d be in a lush beach paradise enjoying sun, sand, and fresh seafood.

There were some storms coming into Dallas, but nothing too severe according to weather.com and we should be able to make our connection in Dallas. Wonderful news for me as someone who rarely travels unless I can get there by car.

The boarding process was smooth and easy. Jen and I had the two outside seats in an extra legroom row and before I knew it boarding was completed. The captain came on and said that we had a 15 minute delay but should take off shortly after a brief mechanical delay. Yay!

Twenty minutes later the captain announced that our flight had to be canceled due to mechanical issues that could not be fixed because the mechanic that had to certify the repair was unreachable. Not the best start, but surely we can get another flight to Dallas and make our connection with two hours between landing in Dallas and our connection taking off…

NOPE. Due to the weather in Dallas several flights were delayed or canceled and the counter ticket agent couldn’t do anything. We went downstairs and Jen got our luggage off the carousel. Outside, I called customer service and the phone agent told me the flight was still going to leave as scheduled. I had just been deplaned and retrieved my luggage. In an unusual act for me, I asked for her supervisor. Thankfully the supervisor understood and began looking for flights the next day to get us to PR.

She found it! There was actually a flight the next day at 6AM which would be about the same route to Dallas and then San Juan. She processed the transfer and I had an email before we ended the call. We would even keep the car rental because we had 24 hours to actually pick the car up. I profusely thanked the phone agent supervisor and Jen and I got on the shuttle to get my car and head home for a nap until the next day. We had been knocked down, but we were definitely not out.

We woke up and drove to the airport, parked, took the shuttle. When we got to the American Airlines baggage check, our dreams were shattered. It seems that with the Dallas weather there were an obscene amount of people now traveling and all trying to get out first thing in the morning – this meant a HUGE line to check baggage. We watched the flights update board as our time slipped away and our flight time passed. Another knock, but maybe the counter agent can help us in some way.

Once we reached the front of the line we spoke to a very nice lady who took pity on us and spent a significant amount of time to find us a way to get to Eugenio María de Hostos airport. It at least got us to the west side of the island near Cabo Rojo. At this point the rental car was gone, but we should be able to get another on this side of the island. The counter agent warned us that it would be a lot of flying, but we didn’t care. At this point we just needed to get to Puerto Rico and enjoy 4-5 days of what we had left for our AirBnB reservation.

Warning – when an airline employee tells you there is a lot of flying they are not fucking with you. Our trip to Puerto Rico took us from St. Louis to Dallas, Dallas to Charlotte, Charlotte to Orlando, and FINALLY Orlando to Eugenio María de Hostos in Mayaguez.

The very kind counter ticket lady called the gate to hold the first flight, rushed our bags to the flight, and we boarded. Finally, our vacation nightmare can begin!