Even the most carefully planned trip can take unexpected turns. Flights get delayed, you can’t access cash from the ATM, or you have minor run-ins at immigration. Most travel hiccups are just that: temporary situations that test your patience and your sense of humour.
But others stick with you, not because they ruined the trip, but because they reshaped it. They’re the stories you tell later. The ones where things didn’t go as planned… the ones that are hard, stressful, upsetting, or even scary in the moment, but turned out okay in the end.
Here are 13 of the most challenging moments from our journey—and what we learned from each one.
#13: The Times We Got COVID
Many thought we were crazy leaving in February 2022, just as the world was opening up again. We left when COVID testing was still required for some international flights, and wearing masks and isolation were common practices.
So, of course, we couldn’t outrun the dreaded virus for long. And at some points, in the first year, it felt like we were collecting more strains of COVID than passport stamps. All in all, one or more family members contracted COVID in five of the twenty-one countries we visited. Luckily, we had mild cases with cold symptoms and fevers. We followed current public health recommendations and recovered quickly. The main issue was the challenges it caused with logistics – having to extend stays, cancel upcoming accommodations and flights to isolate.
Travel Tip #56: Book accommodation with flexible cancellation policies. See Full List.
#12: The Time We Bused to Uyuni, Bolivia
We took an overnight bus from Sucre to Uyuni (and later from Uyuni to La Paz)—our only bus journeys in Bolivia. Though the seats reclined and came with footrests, the ride was anything but restful.
Bolivia is known for its treacherous roads and often hazardous driving conditions. Our bus sped through winding mountain passes, hugging cliffside roads with dizzying drops. I eventually shut my eyes—not because I was tired, but because watching the world fly past at those speeds was too nerve-racking.
We arrived in Uyuni earlier than expected—4:30 a.m.—with nowhere to go. We took a taxi to our hostel, hoping they’d let us in early, even just to crash in the lobby. Thankfully, the host was incredibly kind and found us a small room to rest in until ours was ready.
That morning was bitterly cold (-10°C), and our temporary room had no heat. We huddled together in a single bed, relying on body warmth and layers to stay warm. Still, it beat being outside. We had an incredible experience exploring Bolivia’s Salt Flats and eventually returned to La Paz on another overnight bus.
That’s when we discovered my backpack—tucked under the footrest—had been rummaged through. My laptop, tablet, and sunglasses were stolen, quite literally, from under my feet. It was a frustrating end to our Uyuni adventure, but also a reminder that even the most incredible journeys come with bumps along the way.
Travel Tip #37: Book an extra night when arriving early or leaving late. Having a room ready at 4:30 am—or a place to rest before a midnight flight—can make a long travel day feel a whole lot easier.
Travel Tip #59: Upload photos to a cloud. See Full List.
#11: The Time We Lost Our Bags For a Month
A short flight from Paris to Zagreb turned into a long lesson in patience when our luggage didn’t arrive—and didn’t show up for a whole month. A baggage handler strike meant our bags never left France. After a string of fruitless phone calls and even an in-person visit to the airport, we worried we might never see them again.
We managed in Croatia with replacement clothes, but the loss of the boys’ schoolwork, my writing journal, and a few keepsakes from home that brought comfort on hard days was emotional.
Then, just when we’d given up hope, we got a call—our bags had finally arrived in Zagreb! By some miracle of timing, we were due to fly out of that very airport the next day, heading to Greece. Perfect.
But travel rarely sticks to the script. The day we left Split, a torrential storm rolled in. Roads were slick, accidents were everywhere, and our five-hour bus ride turned into nine. We pulled into Zagreb just one hour before our flight.
Derek and I exchanged a look: do we try to retrieve our bags… or make our flight?
We decided to try for both. We raced into the airport and headed straight for the baggage office—but no one was there. Deflated, we returned to the check-in counter and explained the situation to a staff member. Without hesitation, they sprang into action, escorting Derek through restricted areas to baggage claim.
A few tense minutes later, Derek came walking back toward us, dragging our long-lost bags behind him. We rushed through security and made it to the gate just before it closed.
We couldn’t believe our luck—or the incredible kindness and effort of the airport staff that made it all possible.
Travel Tip #8: Bring essentials in your carry-on. See Full List.
#10: The Time Mason Touched a Wasp Nest
While in Indonesia, one of our biggest adventures was trekking through the Sumatran jungle in search of wild orangutans. Unfortunately, our hike started with a bang—or should I say, a sting.
We set off early, full of anticipation, ready for an eight-hour hike to our overnight jungle camp. But just minutes into the trek, Mason accidentally brushed up against a wasp nest and was stung nine times. Our guides reacted instantly. They ran into the forest, found a particular flower, crushed it, and rubbed the pulp over his stings. Incredibly, the swelling and pain began to fade within minutes. And while Mason was sore and shaken, he bravely pushed on.
Later that day, it was my turn. I slipped down a muddy slope and landed hard on the rocks below, badly bruising my tailbone. It was weeks before I could sit properly again.
The trek was wild, unpredictable, and not without pain, but it also gave us our first glimpse of orangutans in the wild. That day reminded us that adventure often walks hand in hand with mishap, and we wouldn’t have it any other way.
#9: The Time We Tried to Visit the Grand Palace in Bangkok
On our first day in Bangkok, we planned to visit the Grand Palace—but it wasn’t in the cards. First, Jackson got side-swiped by a car in a narrow alley on our way to the bus stop. With a bruised shoulder and frayed nerves, we flagged down a taxi, only to find the driver nodding off at every red light. Just as we neared the palace, he slammed on the brakes, sending Mason into the front seat, giving him a nosebleed. We bailed. After cleaning up, we walked the final stretch—only to be turned away at the gate because my skirt didn’t meet the dress code. SCREAM!
We tried to salvage the outing with a short walk to nearby statues, but gave up soon after and headed back to the hotel for an afternoon swim, vowing to try again another day.
Travel Tip #66: When things go sideways, take a breath, regroup, and find a new plan. Flexibility is key to surviving travel fails. See Full List.
#8: The Time We Got Separated in Thailand
After a long bus ride from Sukhothai to Bangkok, we arrived late at night and broke one of our cardinal rules: never follow strangers who solicit you when offboarding. After wandering away from the bus terminal, our uneasiness grew as we realized the man wasn’t a legitimate taxi driver. We quickly doubled back to the real taxi station. Unfortunately, none of the vehicles there could fit all of us and our luggage, so we split into two cars. With no shared language, our discomfort grew stronger, as we had to trust that the drivers understood where to go.
One car arrived at the destination. The other did not. Fifteen, then twenty minutes passed, and nothing happened. Eventually, the second car arrived and we were reunited. It was a stressful night, but thankfully, we made it through together.
Travel Tip #7: Follow your gut. If something doesn’t feel right. Don’t do it. See Full List.
#7: The Time Mason Learned Pools Can Sting More Than Your Eyes
While staying in Krabi, Thailand, Mason went for a dip in the hotel pool. But what was supposed to be a refreshing swim turned into something else entirely. Mason came out of the water, saying his whole body was stinging, and I could see blood seeping through his sun shirt.
When I helped him out of his swimsuit, I was horrified to find his torso, upper legs, and arms bright red and covered in small bumps. Worst of all, his nipples were bleeding. It turned out the pool had a severe chemical imbalance, and Mason had suffered chlorine burns.
We washed him off, slathered him in cream, and gave him an antihistamine and Tylenol. Things settled down, but he was incredibly uncomfortable for a few days. His nipples continued to bleed on and off, and he spent most of the time shirtless to avoid further irritation.
It was a painful lesson in pool safety—and one that Mason (and the rest of us) won’t forget anytime soon. Needless to say, we avoided that pool for the rest of our stay.
Travel Tip #27: Pack a medical kit. You don’t want to be searching for a pharmacy when illness or injury hits. See Full List.
#6: The Time Kim Wore Short Pants in the Amazon.
This was a mishap that I should have known better. Who goes hiking in the Amazon rainforest in cropped pants and ankle socks?
By the next morning, my legs were covered in angry, itchy bites. Our guide identified them as sand flea bites, and they only got worse from there. The swelling was so painful that it felt like my skin might split open. Then, the bites filled with fluid and oozed for days. It took weeks before my legs fully healed.
If the jungle is full of anything, it’s insects—and they don’t mess around. So, when we say, Travel Tip #52: Wear long pants and full socks on jungle treks. We mean it. I learned the hard way. See Full List.
#5: The Time Mason Got a Concussion
Tiger safaris are one of India’s best wildlife experiences—and at the very top of Jackson’s “must-see” list for our world trip. So, when we arrived at Ranthambore National Park, we were buzzing with excitement. But tiger trekking in India isn’t exactly a smooth ride.
Compared to safaris in Africa and South America, Ranthambore’s roads are rougher, and safety regulations are looser. Paths are uneven and riddled with potholes. There are no seatbelts, and trucks sway dramatically through the thick jungle.
It was here that Mason suffered a concussion after hitting his head on a metal bar. We didn’t realize how serious it was at first, but soon he was complaining of nausea, headaches, and light sensitivity.
We cancelled the rest of our game drives and spent the next few days holed up in our room, letting him rest and recover.
#4: The Time Derek Got Stitches
Sailing along Croatia’s Dalmatian Coast was a trip we had long dreamed about, and it was everything we hoped it would be… except for one major mishap.
A few days into our two-week sailing trip, Derek was helping tie up the boat in a quiet cove when he slipped on some jagged rocks and split open his shin: blood, shock, and a need to get help quickly.
Our captain quickly arranged a water taxi to Hvar Town—a wild ride across the open water in the dark—and got him to a medical clinic where they stitched him up.
The boys were shaken, worried about their dad. And for Derek, the worst part wasn’t the pain or the stitches—it was being banned from swimming for the next week. Stuck watching from the deck as the rest of us enjoyed the turquoise waters of the Adriatic Sea.
Travel Tip #11: Get travel insurance. Check that your policy covers medical emergencies, trip cancellations, theft, and any adventure activities you plan to do. See Full List.
#3: The Time We Got Food Poisoning in Indonesia
What was meant to be five days enjoying the beaches of Bali turned into a tour of the hotel bathroom for three of the four of us. Not long after arriving from Sumatra, Derek, Jackson, and I started to feel unwell—and it all went downhill fast.
The culprit? A&W meals at the airport.
Being that sick while away from home is awful. We were weak, dehydrated, and stuck trying to care for a very ill child while barely functioning ourselves. Jackson was miserable, and it was all we could do to keep him comfortable. Thankfully, we had lucked out with one of the only places on our entire trip that had two bathrooms—otherwise, it would’ve been a total disaster.
Mason, somehow, was spared. He’d gotten sick earlier on the flight—likely just from exhaustion—but it seemed to grant him immunity from the food poisoning that hit the rest of us. Usually, Mason’s sensitive stomach is a travel liability, but this time it worked in his favour. While the rest of us were laid out, he was left to fend for himself, quietly watching TV, making toast, and patiently waiting for us to recover.
Travel Tip #21: Accept that family members will get sick. No matter how hard you try, illness is part of life (and travel). See Full List.
#2: The Time Mason Had Food Poisoning in Morocco
After an enjoyable day exploring the Marrakesh Medina, Mason was hit with the worst case of food poisoning I have ever seen. It was twelve brutal hours of vomiting every 10 to 15 minutes. By morning, he was completely exhausted and dehydrated, but there seemed to be a bit of a reprieve. We packed up and drove to Essaouira, with Mason bravely enduring the car ride.
We thought we were through the worst of it. But that evening, his nausea returned with a vengeance, along with stomach pains and a sudden, high fever. He lay curled up on the floor, crying, leaving us feeling completely helpless.
The one thing that made this even harder? It was just one week into our world trip. When you’re sick, all you want is home. And as a parent, when your child is ill, all you want to do is make it better. The feelings of homesickness hit us hard. And doubts crept in—had we made a mistake taking this trip?
We were fortunate that our Airbnb host was a doctor. We messaged him and within an hour, he and another doctor were at our door. Mason was prescribed antibiotics, and our host personally drove us to a pharmacy to pick them up. That first dose marked the start of his recovery, and our host continued to stop by to check on him every day until Mason was well again.
We were incredibly touched by his generosity and care. In a foreign place, far from home, that kindness meant everything.
#1: The Time We Got Lost in Chobe National Park
Nearly six weeks into our self-drive safari through Southern Africa, we thought we had the hang of it. But the day we left Savuti in Chobe National Park for Khwai in Moremi Game Reserve turned into an eleven-hour rollercoaster of emotion, adventure, and survival.
It started with a promise. We travelled through Botswana’s grasslands and had some exciting animal sightings: A family of elephants, a young lion resting beside an elephant carcass, and a leopard casually crossing the road in front of us. We were floating on a wildlife high.
Then, as dusk approached and we turned toward camp, the terrain shifted.
Just 15 minutes from our destination, the road became a marshy trail. Our GPS pointed us down increasingly muddy tracks—until suddenly, we were swallowed by swampy sludge. With half the truck buried and the tires spinning, Derek somehow got us out. But we’re still haunted by what might’ve happened if he hadn’t.
With our emergency satellite phone and GPS signals failing, we spent the next hour trying and failing to find a passable route.
Eventually, we found our way back to the main road. Now in total darkness, we bumped along the pothole-filled path in tense silence, not sure how much farther we could go.
Finally, a light appeared—a luxury safari lodge. The kind staff called our actual campground and arranged for someone to guide us to our camp.
The stress of the day came from the unknown—the fear of what could’ve happened if we hadn’t made it out. But like many mishaps, it’s a story we’ll be telling for the rest of our lives.
The Mishap We Managed to Miss
As it turned out, not all close calls happened on the road. We unexpectedly found ourselves back home for a month during our travels, and less than a week after returning, Mason needed surgery for appendicitis.
Had we stuck to our original itinerary, we would have been on Cat Ba Island in Vietnam—a beautiful but remote place, a ferry ride away from any major medical centre. The thought of facing that emergency far from home, unsure of the facilities or language, still gives us pause.
It was one of those rare moments in travel where a detour turned out to be a hidden blessing. We were deeply grateful to be surrounded by family, friends, and a medical system we knew. Sometimes the mishap that never happens is the one that leaves the biggest sigh of relief.
Lessons From Abroad
These moments—the tough ones—reveal things you might not have seen otherwise: resilience, teamwork, and the strength you discover by facing challenges together as a family. They are what real travel is all about.
And through it all, the one thing surprised us again and again was the kindness of strangers. From the safari lodge staff who guided us out of the bush, to the women who helped us locate our lost luggage, to our Airbnb host who cared for Mason when he was ill, people went out of their way to help. Their generosity reminded us that while travel may stretch your limits, it also opens you up to the best in humanity.
Ready to Get Started?
Check out these related posts to help plan your World Trip:
• Our 17 Month World Trip Itinerary
• How much does a World Trip cost?
• What’s it Really Like to Travel the World?
• One Month Check-in: Tips on Transitioning to Life on the Road
• How to Involve Your Kids in Planning a World Trip?
