You can spend hours coming up with the perfect travel itinerary, but plans typically never go the way you expect them to. Delays, detours, and last-minute changes come about from time to time, but they usually end up being some of the most memorable parts of the journey. At Swift, our team is full of avid travelers, and we’ve all endured our fair share of unexpected travel experiences. We wanted to share these experiences with you to show that some of the best travel memories are the ones that you never saw coming.
My Most Unexpected Travel Experience: Laurie
On a trip to the Turks and Caicos, my husband Rob and I decided to do a little island hopping. We had plans to stop briefly on a smaller island to pick up passengers, continue on to South Caicos—a quiet, off-the-beaten-path spot where I’d studied abroad in college—and finally land in Provo, the main island. But the journey took an unexpected turn.
Apparently, not all of the islands have jails, so when we landed to pick up passengers, four men in orange jumpsuits, chained together, flanked by armed guards boarded our little plane. No one said a word. The prisoners were ushered to the back of the aircraft, and we quietly took off like nothing unusual had happened.
The flight itself was uneventful, but Rob and I couldn’t stop exchanging wide-eyed glances. For a moment, we felt like we were extras in Con Air: Island Edition. If Nicolas Cage had walked on with a fake southern accent, we wouldn’t have even blinked.
Lesson learned: tropical vacations can bring sunshine, seashells… and sometimes, surprise felons.
My Most Unexpected Travel Experience: Rob
We were on South Caicos (the island part of Turks and Caicos), celebrating a national election we didn’t fully understand, partying with locals who remembered Laurie from her college days on the island. The night was electric, filled with booze and the best fried chicken in the world, the kind of random spontaneous fun that ends with a great idea, like “Let’s get to Providenciales tomorrow for Conch Fest.” Flights? Not happening. But a local guy with a boat overheard our mission and drunkenly said he’d take us, warned it’d be a long ride, told us to meet him at the dock at 8am… it was 2 am. We somehow showed up at 8 not knowing what would happen, and so did five other locals, also hitching a ride, coolers in tow.
The trip started like a dream, glass-clear water, five feet deep all the way, sun on our backs, wind in our faces. Time stopped. Then so did the boat. Turns out, our captain didn’t factor in the extra weight and how that might affect fuel consumption. We ran out of gas, right there in the middle of the ocean, land barely visible. Spotty cell service, the captain trying to call for help, nothing going through. We were officially stranded. That’s when things got weird. Within minutes, everyone was in full survival mode. People were pounding water, hoarding snacks, mentally preparing for their Cast Away era. Laurie and I just sat there, watching it unfold like a reality show gone off-script.
Eventually, a miracle text made it through. A friend was on the way with more fuel. Just like that, the vibe flipped. Water and survival snacks were abandoned, rum was cracked open, the rescue turned into a pre-Conch Fest boat party. We made it, of course. Conch was eaten, drinks were poured, and we even ran into our boat mates later, fully recovered from their five-minute shipwreck drama.
The Life Lesson? When you’re stranded in paradise, don’t panic… unless it gets you to the rum faster.
My Most Unexpected Travel Experience: Shaina
About ten years ago, I took a trip to New York City. I was riding the L train, heading toward downtown Manhattan, expecting just another subway ride through the city. But what happened next turned into one of the most unexpectedly memorable travel moments I’ve ever had.
There was this guy on the train—funny, loud, and unmistakably from Jersey, based on his thick accent and attitude. He was cracking jokes out loud, getting the whole train laughing, and he ended up sitting right in front of me. I couldn’t help but hear every word. Then, out of nowhere, he turned around, looked at me with a smirk, and said, “Watch this.”
What followed felt like a scene out of a sitcom. He started flirting—with confidence and zero hesitation—with a girl sitting across the train. She looked about 19 or 20, clearly out with her family: her younger sister and their dad. They seemed to be on a cheerful family outing. But that didn’t stop Mr. Jersey from laying it on thick. The dad noticed quickly and stood up, clearly trying to send the guy a silent message. But the Jersey guy wasn’t fazed in the slightest—he kept flirting, and what’s worse (or funnier), the girl seemed to like it.
As the train approached the next stop, the father and younger daughter got up to exit. The older daughter stood too, but she was so caught up in the conversation, so glued to every word the guy was saying, that she didn’t exit in time. The doors slid shut before she could step off. The train pulled away—with her still on board, staring at her dad turning red on the platform. The guy from Jersey? He just laughed like he couldn’t believe what had just happened.
That moment stuck with me, not just because it was hilarious and completely unexpected, but because it taught me something too. As a parent, you can get so focused on guarding your kids from others that you forget to keep your eyes on them. That dad kept glaring at the guy, but in the end, it was his daughter who missed her stop!
My Most Unexpected Travel Experience: Alexa
My husband and I were visiting Breckenridge, Colorado, and we wanted to go on a scenic hike. We found a trail nearby, and started walking up it. We were hiking for 15-20 minutes, and saw nobody the entire time. It turns out that the trail was actually closed for the weekend, as they were setting up for the Spartan Race! It was really cool though because we got to see all of the obstacles up close and personal, without actually having to take part in the grueling race. One obstacle I would have loved to try is the spear throw, and one that I would happily stay away from is the burpee station!
My Most Unexpected Travel Experience: Paul
On a trip to Moscow around 22 years ago, I had the surreal experience of performing a series of concerts that felt straight out of a spy novel. Between gigs, I was chauffeured through the city in sleek black cars—former KGB vehicles—adding an unexpected Cold War flair to the adventure. The contrast between the raw energy of the performances and the shadowy elegance of those vintage rides made the entire journey unforgettable, like stepping into a different era for a few electrifying days.
What was your most unexpected travel experience? How did it change your perspective of travel?
