When Your Trip Doesn’t Go as Planned (Because It Probably Won’t)
You can plan for months — research hotels, color-code your itinerary, pre-book tickets, even pack pack your clothes by day — and still, something will go wrong.
It’s practically a travel guarantee.
Over the years, I’ve learned that some of the best (and worst) travel memories start when the plan falls apart. Sometimes it’s a minor hiccup. Other times, it’s the kind of chaos that makes you want to cry in an airport bathroom. Either way, those moments often become the stories we remember most.
Here’s a collection of my personal travel misadventures — and what I’ve learned along the way.
1. The Tarmac Test of Patience
Just recently, we sat on the tarmac at LaGuardia for three hours, missed our connecting flight, and ended up spending the night in St. Louis just to get home the next day. Luckily, this was the end of our fall break and not the beginning — but it was still one of those moments that tests every ounce of patience you have.
These situations happen nearly every day, especially with weather delays and short-staffed airlines.
Tips:
Pack a “delay survival kit” in your carry-on — snacks, chargers, a water bottle, and something to help you decompress (book, podcast, or downloaded Netflix shows).
Stay kind to the gate agents. They’re dealing with a hundred frustrated travelers, and kindness often goes a long way.
2. The Sick-Kid Scenario
No parent ever wants the middle-of-the-night-wake-up to a child standing beside your bed saying, “I don’t feel good.” What about when it happens while you’re on a trip? On a nine-day, four-state road trip around New England, this happened to us. My oldest got sick. Instead of letting it ruin our entire trip, we pivoted. My husband took our youngest out to explore while I stayed back at the hotel with our sick son. Not exactly the dream vacation we had pictured.
At first, I was devastated. All the carefully planned excursions? Gone. But once we surrendered to it, something shifted. We slowed down, ordered room service, watched movies, and snuggled under blankets while enjoying amazing views of Boston Harbor. It wasn’t the trip I planned, but it was the trip we needed.
Tips:
Pack a small “just in case” kit — fever reducer, electrolyte packets, wipes, and a change of clothes for everyone.
Check policies for changing your dates or times, and consider travel or event insurance for high-dollar items.
Remember: no itinerary is more important than good health and rest.
3. The Lost Credit Card and Phone Adventures
Losing things on the road seems to be a rite of passage. I once dropped my credit card somewhere in Dollywood. Another time, I dropped my phone in Lake Ontario. Being in another country without a cell phone? Not for the faint of heart.
We were planning to drive two hours to meet my husband, who was joining our adventure. Without Google Maps, we got turned around more than a few times in an unfamiliar city, eventually pulling into a fire station to beg the firefighters for directions (and a bathroom). I felt like we had been transported back to the 1900s.
Tips:
Carry a backup card stored separately and a prepaid card for emergencies.
Take photos of your passport and card numbers before you leave (stored securely).
Always have a backup plan for navigation: a paper map and key addresses can save the day.
4. The “My Account Was Hacked While Traveling” Plot Twist
Twice while traveling, I’ve gotten that call from my bank — the one that starts with a polite greeting and ends with, “Your account has been compromised.” It’s stressful enough at home, but it’s even harder when you’re traveling — suddenly you have to freeze your credit or debit cards, juggle backup payment methods, and figure out how to pay for meals, hotels, and gas.
Tips:
Monitor your accounts regularly while traveling. Many banks send instant alerts.
Avoid public Wi-Fi for banking or sensitive information.
Freeze or monitor your credit if you’re traveling internationally.
Carry a backup card stored separately.
5. The Case of the Missing Luggage (and the Missing Car Seats)
Nothing tests your patience quite like watching the luggage carousel spin… and realizing your bag — or worse, your children’s car seats — didn’t make it.
We once landed after a long day of cross-country flights, only to discover both of our car seats were still enjoying a layover somewhere else. Considering our final destination was an hour’s drive from the airport, this was not great news. After several deep breaths (and maybe a few silent prayers), we managed to rent seats from a nearby car rental agency. Not ideal, but it got us safely on our way.
And we’re not alone. On another trip we took with a close friend, she realized — too late — that her suitcase, complete with her work laptop, was still riding around Chicago in the back of a taxi. She spent the entire weekend chasing leads trying to get it back. Spoiler: she never did get it back.
Tips:
Always pack essentials — medications, chargers, one outfit, and toiletries — in your carry-on.
Take a quick photo of your bag (and your car seats!) before checking them so you can describe them easily if they’re lost.
Use luggage trackers like AirTags or Tile to help locate wandering belongings.
File your lost baggage report immediately and keep receipts if you have to buy replacements — most airlines will reimburse reasonable costs.
Stay calm and remember: it’s usually delayed, not gone forever.
6. The Big Picture: Let Go of Perfect
Every traveler eventually learns this truth: perfection isn’t the goal — presence is.
The cancelled flight might lead to an unplanned adventure. The sick day might bring unexpected connection. The lost wallet might introduce you to the kindness of strangers. And the missing suitcase? Well, that one might teach you to travel a little lighter next time.
It’s okay to grieve the plans that fall apart — but don’t miss the story that’s still unfolding. Travel, like life, is full of detours. The best thing you can pack is flexibility (and maybe a backup credit card).
Final Thought
When things go wrong — and they will — take a deep breath, laugh when you can, and remember: someday these chaotic moments will make the best stories.
Even the three hours on the tarmac.
Even the firemen who gave directions.
Even Lake Ontario.
And yes, even the lost suitcase in the Chicago cab.
Travel may never be perfect — but it’s almost always memorable.
