When Travel Goes Wrong 🙃
No matter how experienced you are, travel will almost always throw you curveballs
Travel has a way of making us feel glamorous one minute, like sipping Aperol spritzes on a sun-drenched patio in Italy, and completely wrecked the next, like the time I slept on the floor of JFK from midnight to 4:30 a.m. with my backpack as a pillow and a hoodie for warmth, waiting for security to open for a 6 a.m. flight.
That was not the kind of red-eye I had in mind.
Or the time I confidently grabbed my bag off the carousel at JFK, hopped in a cab to Manhattan, checked into my hotel, and discovered—thanks to a call from the airline—that I was now the accidental owner of someone else's luggage (eek!!). Another hour-long cab ride back to the airport later, I was reunited with my actual suitcase. Lesson learned: always double-check the tag, and for the love of travel, put a name label on your bag (and perhaps an Apple AirTag, too!). It's true—so many suitcases look alike, especially after a long flight.
The truth is, no matter how seasoned you are, travel throws curveballs. Missed connections, flat tires, hotel reservations that mysteriously vanish, and yes, someone else's nearly identical luggage rolling away in your hand. These moments aren't fun, but they're part of it. And over the years, I've learned that the best travelers aren't just the ones with TSA PreCheck and packing cubes. They're the ones who can keep calm, stay flexible, and maybe even laugh when it all goes sideways.
Here are some everyday travel fails and how to handle them without totally losing it. 🤪
1. Missed Flights (AKA airport cardio)
You arrive at the gate breathless, sweating, and convinced you made it—only to see the plane pulling away. That sinking feeling? Brutal.
What to do:
Head to the airline counter and call customer service while you're in line (this is key!). Ask nicely if they can rebook you—sometimes they can, at no extra cost. And if you purchased travel insurance in advance (I recommend Allianz or Faye) or booked with a reliable credit card; even better.
Lesson learned:
Give yourself more buffer time than you think you need, especially at places like LAX, O'Hare, or Atlanta, where "short layover" often means "you're not making it."
2. Sleeping in Airports (JFK Edition)
One time, I ended up being stuck overnight at JFK. Security shuts down from midnight to 4:30 am, so I had no choice but to curl up on the linoleum floor near Terminal 4 with a group of strangers as if it were an unfortunate sleepover party.
There is no food, no lounge access, and no quiet—just a chorus of cleaning crews and bad vending machine snacks.
What to do:
Download the "Sleeping in Airports" app (yes, it’s a thing!), carry earplugs, and keep a scarf or hoodie handy to use as a makeshift pillow. If you're traveling through an airport where this could happen, plan for the worst.
Silver lining:
I made my 6 a.m. flight. Barely. But I've never been more excited for airplane coffee in my life.
3. The Great Luggage Mix-Up
Speaking of JFK, after a long flight, I grabbed my bag and got out of there fast—too fast. It wasn't until I got to my hotel in Manhattan that I found out (thanks to a panicked call from the airline) that I had taken someone else's suitcase. Cue a mortifying return trip to the airport in a yellow cab, where I sheepishly swapped bags and apologized to the person stuck in the same mess on the other end. Oy!
What to do:
Before you grab a bag, double-check the name tag and luggage tag to ensure they match. If your suitcase is standard (black roller, anyone?), consider tying a ribbon on it or getting a brightly colored tag so it stands out. And put your contact info inside and outside the bag. Also, consider using Apple AirTags.
Lesson learned:
No matter how tired you are, do not go on autopilot at baggage claim.
4. Broken-down cars in the Middle of Nowhere
Driving Highway 1 along Big Sur? Magical. Until your rental car dashboard lights up like a Christmas tree, and you lose cell service near Bixby Bridge.
What to do:
Always have a paper map (old school, I know, but so helpful!), and download offline Google Maps before your trip. If your rental company has roadside assistance, use it. If not, wave someone down and channel your inner pioneer spirit. You're not the first person this has happened to, and you won't be the last.
5. Wallet or Passport Gone Missing
Whether it's a pickpocket on the New York City subway or your bag "disappearing" from a café in Barcelona, losing your wallet or passport is a massive headache.
What to do:
Before you leave on your trip, take photocopies of your ID and passport, and store them in your email or a secure cloud storage service. Cancel credit cards immediately.
If it's your passport, report it immediately by filling out the DS-64 form and contact the nearest U.S. embassy or consulate ASAP—they can often issue an emergency passport to get you home.
Pro tip:
Keep one credit card and some emergency cash in a separate pocket or bag. You never want to be left stranded.
6. Overbooked Flights, No Room at the Hotel
You booked months ago. You checked in. You have your seat. And somehow, the airline still gives it away.
Or your hotel in New Orleans claims they "don't have a reservation under that name." Sigh.
What to do:
Ask if the airline can rebook you on another carrier or upgrade you. If you're involuntarily bumped from a flight, you're legally entitled to compensation—don't be afraid to ask.
For hotels, always call the day before to reconfirm your booking. And if you're stuck, ask for a rebooking at a sister property or a discount.
7. Getting Sick on the Road
The street food you got for lunch seemed like a good idea until about three hours later (ugh, food poisoning the worst!). And coming down with the flu or another illness while traveling can totally taint your trip.
What to do:
Always pack basics like Imodium, ibuprofen, dramamine, and electrolyte packets. Pharmacies are often your best friend, especially abroad. And don't wait to see a doctor if symptoms worsen.
When traveling abroad, remember to research the local emergency numbers (such as 112 in Europe or 999 in parts of Asia) and save them in your phone. Also, identify the location of the nearest hospital and U.S. embassy or consulate.
Also, a friendly reminder to use bottled water for brushing your teeth and drinking in places where the water may not be 100% safe.
What Travel Teaches Us ✨
When things go wrong—and they will—it's not always about fixing it. Sometimes, it's about how you handle it. Travel teaches patience when nothing's in your control, flexibility when your plans fall apart, and resilience when you realize, "Okay, I guess I can sleep on the floor at JFK and still function tomorrow."
It also teaches humility. It's like showing up at your boutique hotel in Nashville only to discover that your reservation doesn't exist. Or realizing you left your wallet in a cab in Chicago. Or, yes, accidentally taking home someone else's luggage and having to haul it back through city traffic.
So next time your rental car dies in the middle of the desert, or you're stuck overnight in Denver with nothing but vending machine snacks and a dying phone, remember: this isn't a failure. This is the part of the story you'll tell at parties or over drinks with friends.
While you’ll want to remember to pack all your essential items in your carry-on, don’t forget to pack your sense of humor. You’re going to need it. 😜
Happy Summer Travels!
Love these tips. One thing I would add to the lost ID point. This happened to me in Chicago when my wallet was stolen. TSA didn't accept any digital copies of ID. They needed physically prints! But I had some medication on my with my name and they accepted that as my ID to return back to my home state.
I had my phone stolen out of my pocket in a small shop while in Paris. On a solo trip. I had to navigate my way back to my airbnb without any way of communicating, and without a map. It was about a 25 minute walk. But it felt better and safer than the metro at that point.
Eventually I did make it back and immediately got on my ipad to “brick” my phone but it was a lost cause. I also went the very next morning to the Apple store for a very expensive souvenir.
Later my French friends said that having your phone taken there is like a rite of passage. Lesson learned about keeping my phone safer!!