My Top 3 WORST Travel Moments of 2021

I honestly hoped I would never have to write a post like this. And while I technically don’t need to, I want to keep this site as real as possible. I try to keep most of my posts positive, upbeat, and full of good information. But every now and again, things don’t go the way that I hope. Thus, my top 3 worst travel moments of 2021 was born.

Part of the joy of travel is the spontaneity that comes with it…but it also can lead to some rather uncomfortable moments.

Fortunately my inaugural list this year is short, and even more so that each moment occurred during different trips.

Oh my goodness, could you imagine if they all happened within the same weekend trip? I mean, it can happen, but hopefully not.

Here are my top 3 worst travel moments of 2021, and may they all serve as learning experiences for us all.


A Sleepless Night in Puerto Rico

Puerto Rico 2021 was a redemption trip for me, hopefully to wipe out my 2016 experience (read about that here)…but it didn’t start out very promising.

Traveling during the madness of having to get tested and closures and all the uncertainty brought on since 2020 was difficult enough once travel restrictions loosened. But add on the pressure of redeeming a location and the midnight arrival time after a long travel day…everything felt like it was against me from the outset.

When planning my trip to Puerto Rico, I wanted to start off by exploring the south and west coasts of the island, and then finish my trip in Old San Juan. But since I was scheduled to land in the San Juan airport around midnight, I booked a night in the Conturce Hostel just a short drive away from the airport. It was inexpensive and had great reviews on multiple hostel websites. Seemed like a slam dunk for a place to crash for a few hours before heading south.

I DO NOT RECOMMEND THIS HOSTEL!

After everything was booked, I contacted the hostel and alerted them to my arrival time. Most hostels have office hours during traditional business hours, and I needed to make sure that I was going to have access to the hostel. I received an email from their staff, stating that 24 hours before my check-in time I’d receive another email with my entry key code and room assignment.

Perfect.

I love it when places have automated self check-in for after-hour arrivals. It takes off some of the pressure of arriving in a new location. I knew that I’d have to clear medical protocol at the airport, then go get my rental car, so who knew how long that would take?

The evening before I was scheduled to board my flight, I hadn’t received the promised email. I was within that 24 hour window, so I shot off an email to the hostel again, asking for the promised email with the necessary information. I reiterated the fact that I’d be arriving after midnight and needed to know how to access my paid-for bed.

I went to bed that night without a response. Not a big deal. Puerto Rico was a few hours ahead of me, so I assumed that the email reached the hostel’s inbox during off-hours. I’d check again in the morning.

Well, the morning arrived without an email from the hostel. I emailed them again, pleading for the login information, letting them know that I would be on an few airplanes for the rest of the day and needed a response.

Bad news – I arrived in Puerto Rico without the information I requested.

I got through the medical checks, picked up my rental car, used the restroom one last time (important point, as you’ll soon learn), and decided to just head to the hostel. Maybe if I can get there, someone would let me in and help me figure out where to sleep?

After a quick drive, I found the hostel and parked for a minute to scope it out. The door was barred and a keypad shone brightly next to it, indicating a key code was necessary. I watched a few people walk by, hoping that one of them was going to start punching in their code.

I started calling the numbers listed on the hostel’s website, hoping that someone would answer. I texted the number, left voicemails, and sent another email.

It was all for naught. Nobody responded, picked up, or answered me. At this point, it was almost 2am.

So I was faced with a decision. Do I spend hundreds of dollars securing a hotel room for a few hours, blowing my travel budget out of the water, or do I try to find a safe-looking street to park the car so I can sleep for a few hours?

Instead of paying $300ish for a few hours, I opted to find a street a few blocks away from the hostel, and attempted to sleep in the rental car. I tossed and turned, opting to keep the windows closed to keep out the bugs, but suffering heat and stagnant air instead.

Finally around 7am, I couldn’t take it any more and got out of the car for a walk. I needed to fully stretch my short legs and get the blood circulating again, also looking for a place to use the restroom. While I didn’t find any, I started the journey south to the town of Ponce. About halfway to the other side of the island, I tried yet again to find a toilet.

With the state of the world and businesses being closed, my options were thin. I’d normally pop into a fast food restaurant, but even those were locked down. In the end, I could barely straighten myself up and ran into a local Walgreens. Using broken Spanish, I pleaded with the employees to let me use their staff restroom.

Feeling lighter, happier, and slightly dehydrated, I walked back to my rental car, vowing that I wasn’t going to let these first few hours color my experience negatively. This was a redemption trip, after all. No matter how crappy it started.

I’m happy to say it only got better.

But I never heard back from that stupid hostel.

My Top 3 WORST Travel Moments of 2021 - drone selfie on isla caja de muertos
Snorkeling tour to Isla Caja de Muertos, Puerto Rico

I Almost Missed a Flight

My second trip of 2021 was a week-long trip to Oahu. To take advantage of a flight deal, I had a layover in LAX, which is never a big deal. After my first international flight where I only allowed myself a 45-minute layover in Amsterdam, I learned to give myself a good buffer of time, just in case.

This was the first time I’d be flying with American Airlines in years, and they let me down from the beginning. My flight ended up getting changed multiple times, with finally landing on having a 40-minute layover in Phoenix, Arizona.

Although it was a domestic flight, I was already a little on-edge for having such a short layover. The travelsphere of 2020 and 2021 has changed so drastically, so having a larger buffer is always helpful. I checked the gates I’d be arriving to and the one that I’d have to transfer to, thankfully relieved that they were next to each other.

We landed in Phoenix on time, but wound up sitting on the tarmac seemingly forever. Okay, I’m being dramatic. But when you have a 40-minute layover and you’re stuck on your airplane for 30 minutes, you start to sweat a bit.

There’s nothing worse than being stuck on an airplane in an overcrowded airport, helpless as you receive notifications from your airline app, alerting you that your connecting flight was boarding.

As the clock counted down without our airplane moving, I became acutely aware that I might miss my connecting flight. Phoenix is NOT a good substitute for Honolulu, no apologies given.

I was quickly made aware that more than half of my flight was trying to make the same connection that I was. Surely they’d hold the plane, right?

When we finally pulled into our gate, most of us hopped up, grabbed our luggage and sprinted down the gangplank. Sweat poured down our brows as we skidded to the next gate, thankful that it waited for us.

My takeaways: don’t fly with American Airlines, stay away from Phoenix, and have a longer layover than you think you need.

My Top 3 WORST Travel Moments of 2021 - picture at the lanikai pillbox with the ocean in the background
Lanikai Pillbox, Oahu

Driving on Fumes in Interior Alaska

Rounding out my worst travel moments of 2021 list is a bad call I made when road tripping through interior Alaska.

My friend Ashley and I traveled to Alaska to see the northern lights, kayak amongst glaciers, and to road trip into the backcountry. We’ve traveled a lot together before and have hundreds of miles already under our belts together, having road tripped to Calgary, Idaho, and the Extraterrestrial Highway to name a few.

We did our research and chose our route from Fairbanks to Anchorage and then back again, completing a large circle through the middle of Alaska.

I am a seasoned driver. I don’t tend to get stressed out or phased by much. But I am human and every now and then, I’m reminded of that particular fact.

Driving in the Alaskan backcountry is unlike any other place I’ve traversed. Cell service is weak if you happen to have it at all, road conditions can be unpredictable, the weather can be just as so, and there’s never a sure sign when the next fuel station will be.

We were driving along and came to a major junction for our trip, and our fuel tank was about 2/3 depleted. Under normal conditions, I would try to keep the tank fuller than half. We rocked up to the gas station at the junction and found it to be packed. I had no idea that there were so many other vehicles on the road, given that we rarely saw anyone.

I chose to bypass this fuel station, stating that there was a sign for another one a few miles up the road.

Do you see where this is going?

Newsflash: there wasn’t a fuel station. So we kept driving. Against all instinct. Until we passed the point of no return – where we wouldn’t have enough fuel left in the tank to backtrack to the packed fuel station.

Surely there would be a fuel station coming up, right?

As I kept driving with a place to turn off, turn around, or even really stop, I watched our gas tank slowly deplete.

And then the light came on. No, not the figurative one where I have a brilliant idea. The one that indicates we have 30 miles to empty. Cue the panic.

I’ve never had a panic attack before, but I am almost certain I experienced my first one while behind the wheel of a rented SUV in the Alaskan interior. Normally I’m the one having to calm down my travel partners, but not this time.

I started praying as hard as I could, asking for a miracle.

Spoiler alert: this story has a happy ending.

With only a few miles left until empty and no cell service, I rounded a corner and saw a battered brown sign that had a picture of a tent, a restroom, and a fuel pump on it. Up ahead was a little fuel station with 2 pumps, a weathered shack attached to an even more weathered barn, surrounded by signs of a campsite.

HALLELU…wait…

I pulled up to the fuel pump that resembled something from the 1950s, only to find that the handle to the pump was pad-locked. Wait, what?

I ran up to the shack and my heart sunk. The sign on the door said that the fuel station was closed. I pounded on the door, ready to do whatever I needed to get some fuel.

Nothing.

I turned, dejected, and started back to the car, when a heavenly voice rang out.

Well, not quite. She had the voice of a lifetime chain smoker with a rasp that would rival Chandler’s dad, but it was music to my ears. She graciously handed me the keys to the pump and simply asked me to let her know how much it was.

Marveling about the trust this woman had in me for being honest, I’d never been so happy to overpay for fuel in my life.

My Top 3 WORST Travel Moments of 2021 - ashley and I smiling in front of denali mountain
Ashley and I with Denali peak in the background, at the end of our road trip

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