At about midnight of our second (third technically) day of vacation we landed in Puerto Rico near our AirBnB. There was another canceled flight in the middle of our day of the airports, but we begged a counter ticket person and got rushed onto another connection and made it. Also, at one point Jen was seated behind me on a flight and I elbowed her in the eye while getting my carry on down so we could rush to a connection. THAT resulted in a fuck you look and profuse apologies from me. :shrug:

Feeling relief after landing, it was weird to me to deplane using stairs. I’ve always used larger planes that board and exit using jetways. I remarked to myself that I must be living in Casablanca or at least the 50’s. It was funny in my head.

We walked into the airport with our carry on bags and backpacks to retrieve our two checked bags. Exhausted and ready to get a taxi to the condominium, we waited and waited. Finally the bags started rotating around and everyone started grabbing and heading out the door. Most people were locals or had people picking them up. Lots of celebratory hugs were had and we were feeling happy too having made it to our island paradise.

After about 20 minutes, with most people cleared out and the same bags circling the carousel we realized that somewhere in our 4-5 flight day (depending on if you count the canceled flight in the middle) our checked bags didn’t make it to Puerto Rico.

The counter lady was very helpful in helping us file a lost luggage claim and stepped us through the whole process. How many bags, what were the contents, what flights were you on, names, destination address… It’s annoying but understandable. When travel advisors tell you to always pack a change of clothes in your carry on/personal item – LISTEN TO THEM. Thankfully we did. Jen gets full credit for that. I was going to skip it because I’ve never had anything lost nor delays. Quite out of character for Mr. Plans-everything-to-the-last-detail, but we all make poor choices on occasion.

So we grab our bags and head outside to vape. On our way out we pass the car rental counters and I stopped to check on getting a car. After about 5 minutes I wonder where the personnel are at. “Oh, they closed a couple hours ago” I’m told by a kid who has an airport name tag. Apparently they just leave the lights on for fun. We head outside and look around for a cab while getting our nicotine fix.

Crickets.

Some older disheveled men and some kids from the area that work at the airport are hanging out under the canopy. The kids are vaping too and we chat in between their personal conversations. They were kids to me, but probably 16-25 in reality. One was even nice enough to let me get some vape juice since my main bottles were in the checked bags lost to the airport gods.

Finally we asked them about taxis and were told they wouldn’t start running again until about 6am. At this point we’ve been traveling in some way for about 19 hours. FML. The youngest of the kids offers to call his uncle who drives a taxi to take us to the condominium. “It won’t be cheap” he warned us, but I ask for a price before saying yes and have him call. $100. SOLD.

15 minutes of the old man trying to figure out how to steal our bags or jewelry (the kids tipped us off to the guy’s history), our taxi arrived and we got in to relax and get to a comfy bed. Off we zipped.

If you’ve never been to PR, be warned that speed limits are suggestions and traffic lights are optional – especially at 1am. We zipped along to who knows where on a foreign (to us) island sometimes on back streets. It was completely possible that our organs were about to be harvested or perhaps we were going to be robbed and dumped in a ditch. No telling. I did have the address of the condo put into my phone and the route did seem to be heading there so I let it ride.

We got to the gate of the complex and the guard took some time but found the keys for us to get inside the condo. He buzzed us through. We got to the unit, unloaded our bags, and thanked the driver profusely.

We got inside, generally got settled, and crashed.

That view is actually exactly what we had from our balcony. The place was brand new and looked immaculate.

Here is an image of the bathroom. This becomes relevant later.

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!