Why do I love travel? It’s one of the few activities where I expect the sh*t to hit the fan. Flights get delayed, luggage gets stolen, and sometimes you break your favorite pair of sunglasses by sitting on your backpack. For a Type A personality, you might expect the messiness of travel to drive me crazy. In truth, though, traveling brings out the sunny optimist in me. When I’m traveling, I’m flexible. Eventually, I find the humor where there were initially tears.
I love traveling because it’s all upside. If I have an amazing trip with no problems — beautiful. Now that’s a vacation! If there are minor hiccups, I think: okay, I’m just paying a little tax to the universe. I expect to mess up, to take the downtown train instead of the uptown train in a new city. It’s a learning curve, and I know I’ll get where I’m headed eventually.
If something goes really wrong (discounting serious illness or injury), that’s where you get a great travel story. To prove to you my perspective, I’m sharing one of my “worst” travel stories.
San Juan, Puerto Rico
Have you ever had those experiences where everything that can go wrong does go wrong? That was the beginning of my trip to San Juan, Puerto Rico. I had just started my full-time job, and I was finally taking a vacation. This was my first time putting in PTO, and I felt oh so grown up doing it. Living in New York City, Puerto Rico felt like a great choice: a quick flight, sunshine, and stunning beaches. I packed my bathing suit, a few sundresses, and A Room of One’s Own to read at the beach. I was ready for a week of relaxing in the sunshine.
I checked into my Airbnb and noticed that it was a bit smaller and darker than the pictures suggested online. Excited by the sunshine and salty breeze outside, I decided not to let it derail me. I spent the first two days swimming, reading, and enjoying the lattes in nearby cafes.
On the third day, I knew it was going to storm in the afternoon. I grabbed breakfast at a café and headed home as the clouds began looking angry. When I got back inside the Airbnb, I saw the largest cockroach of my life scurrying across the living room. Quick sidebar: in college, I was the only roommate not afraid of bugs, the designated pest control. (Pro tip: do not crush cockroaches—use spray or traps.) Without going into detail, I reprised my college role. Helping my roommates is one thing; sleeping alongside creepy crawlies on vacation was another.
I immediately started packing my bags and looking for another place to stay. Naturally, all of the hotels were wildly expensive. I eventually found another Airbnb within budget—this time in downtown San Juan instead of near the beach. But hey, there was no mention of bugs in the comments, so things were looking up.
I contacted Airbnb support about the situation. The owner of the apartment refused to cancel my stay. The customer support team took pity on me, though, issuing a refund after sending them proof of the cockroach. By the time I finished sorting the logistics, it was torrentially raining—thunder, lightning, palm trees bending angrily in the wind.
Within 42 minutes, I was packed and in an Uber, heading across the city. Just the walk to the car left me drenched, but I was proud of how quickly I’d recovered from my first real travel fail. The drive took 20 minutes, and I admired the colorful architecture of downtown San Juan. Once we pulled up to the new apartment, I grabbed my backpack and stepped out of the car, circling around to retrieve my suitcase from the trunk.
Before I could open the trunk, the Uber sped off with my suitcase still inside. My thoughts immediately spiraled: Was this an accident? Did my favorite Beis suitcase just get stolen? Do I have to buy an entirely new summer wardrobe? Mostly, I was just thinking in expletives.
In the pouring rain, I took off sprinting after the Uber. Important detail: downtown San Juan has cobblestone streets. Running on slick white stone with my backpack wasn’t helping me gain on the car. After four blocks—past a historic church, clusters of tourists, and souvenir shops—the Uber disappeared. Soaked and admitting defeat, I walked back to the Airbnb. That’s when I reached into my pockets and realized my wallet was gone too. I retraced my steps from my very dramatic 600-meter dash. Nothing. Back in the apartment, I laid out everything I still had: my phone, chargers, medicine, sunscreen, Airbnb keys, water bottle, and the clothes on my back. No wallet. No luggage.
Perfect. Absolutely perfect.
Trying to stay calm, I decided I could have a breakdown after I solved the problem in front of me. Deep in the Uber app, I found the lost-item callback feature. For $20 (major side-eye), Uber will attempt to send your driver back—if the driver agrees.
So, I waited—and spiraled.
What if I couldn’t get my wallet back? How would I fly home? Could I just buy a few tourist outfits and fly home with my backpack? But my favorite bathing suit was gone! Once I googled “How to book a consulate appointment,” I stopped myself. Overthinking was not helping.
I finally paused long enough to notice the new Airbnb. The apartment was adorable with red tiled floors and a swinging seat hanging from the ceiling. By the time I had calmed down (and cried), I got a frantic message from the Uber driver. He was outside and very apologetic for driving off with my luggage. Thank goodness! I headed downstairs and used my limited Spanish to sincerely thank him for bringing back my bag. We searched the car for my wallet—no luck. Still, that was one problem solved.
I felt my luck start to turn once I had my bags back. I had forgotten about my Airbnb messages. Miraculously, the host from the first apartment had found my wallet in a storm drain in front of her house. It seemed that during the chaos of carting my luggage through the storm, the wallet had fallen out of my pocket. Despite the bug incident, she agreed to leave it in her mailbox.
I couldn’t believe how lucky I was. I grabbed my backpack for one more round trip to the beach to pick up my wallet.
Once I got home, what was my solution to all of this? A cocktail with lunch. It could have been five o’clock nowhere—I was having a day.
What I Learned
Every travel fail teaches you something, even when it doesn’t feel like it in the moment. Here’s what this story taught me:
- One Problem At A Time: It’s easy to feel overwhelmed when thinking about all of your problems together. It would have been easy to think: “Why is this all happening to me, can’t I get a break?” But once I started tackling my problems individually, they got solved. I could focus my energy on one task and keep my mind from spiraling.
- Find Humor In The Worst Moments: While I was sprinting down the street after the Uber, I had a thought: How comical would it be if I tripped right now? Not that I wanted to get hurt, but that this moment felt like the plot of a Looney Tunes cartoon. How hilarious and insane was this? By the time I stopped sprinting, mascara running in the rain, the situation was hilarious. Why cry when laughter is available?
- There’s Always A Silver Lining: After sorting this clusterfu*k of a morning, I really appreciated the rest of my trip. Relaxing in the sun, swimming in the ocean, reading my book, I didn’t take any of those moments for granted. I had all my things, a nice place to sleep, and a gorgeous city to explore.
San Juan was the first trip where things truly went wrong for me — and I handled it better than I expected. Traveling isn’t just the places you see, the food, the architecture. It’s also learning about yourself. That confidence — the kind you build outside your comfort zone — is the real reason I love to travel.
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