Unconventional Journeys: How ‘Ill-Advised’ Family Travel Forged Resilience and Wonder in a Young Explorer

I have a long track record of making ill-advised—occasionally unhinged—family-travel decisions. This philosophy, born from a deeply personal journey into motherhood, has shaped a unique upbringing for my son, Julian, proving that the most memorable adventures often lie beyond the conventional. While many parents meticulously plan child-friendly resorts and predictable itineraries, I’ve consistently chosen paths less traveled, embracing the chaos and unexpected challenges that inevitably arise when exploring the world with a young child.

My journey into parenthood itself was a deliberation. I waited a long time to have a child, unsure if I possessed the inherent qualities of a mother or even truly desired the role. This initial uncertainty, however, evolved into a conviction that fear should not dictate life’s choices, especially not Julian’s. While parenthood has naturally recalibrated my perception of risk, I refuse to let trepidation call the shots. Sometimes, plans unravel spectacularly, but I’ve learned to distinguish between a difficult trip and a truly bad one—a crucial lesson that has become the cornerstone of our travel ethos.

Julian’s inaugural interstate trip was a testament to this unconventional spirit. At a mere five weeks old, he was bundled up and transported to Wisconsin for an ice-fishing expedition. While friends and family might have questioned the wisdom of exposing a newborn to the harsh elements of a Midwestern winter lake, for me, it was an early declaration: our lives would not be confined by typical expectations. This early plunge into the unusual set the tone for future escapades that would raise eyebrows and test the limits of what many considered sensible.

At 20 months, with Julian barely out of infancy, I embarked on an ambitious 23-day solo journey with him through Oman, Tanzania, and the United Arab Emirates. This wasn’t a leisurely resort hop; it was an immersive, rugged exploration. We navigated the vast, shifting dunes of Oman’s Wahiba Sands and traversed the ancient, craggy peaks of the Hajar Mountains by road. From there, we jetted off to the plains of Tanzania for a safari, an experience typically reserved for older, more composed children. Friends were convinced I had lost my mind, while my husband, perhaps wisely, offered his blessings and remained home. The logistical complexities of solo parenting a toddler through diverse cultural landscapes, managing long travel days, and adapting to ever-changing environments were immense. Yet, witnessing Julian’s wide-eyed wonder at desert landscapes and exotic wildlife solidified my belief that these experiences, however challenging, were invaluable.

A year later, our adventures escalated dramatically. Julian and I embarked on an epic 88-day odyssey, spanning 14 countries across six continents. This grand tour, designed to immerse him in a kaleidoscope of cultures and environments, pushed boundaries even further. Our stint in India, in particular, ignited a flurry of concern among family members, who envisioned the overwhelming crowds and sensory overload of the subcontinent as unsuitable for a young child. However, places like the ancient, spiritual city of Varanasi and the bustling metropolis of Delhi proved to be unexpected havens. In the glorious, cacophonous symphony of sights, sounds, and smells, Julian’s inherent loudness, which might have drawn stares elsewhere, barely registered. Amidst the vibrant chaos, I found a surprising sense of liberation and could, for once, truly exhale. It was in these seemingly "unsuitable" environments that Julian, a naturally energetic child, thrived, his curiosity ignited by the sheer vibrancy of life around him.

Sometimes, even the best-laid plans go hilariously awry, transforming potential disasters into cherished family lore. When Julian was three, I took him to the legendary Indy 500, an event synonymous with speed, noise, and massive crowds. Thanks to my job in media, we enjoyed enviable perks: a police escort, a VIP suite offering prime viewing, and even pit access, allowing us a rare glimpse behind the scenes of professional racing. I, the seasoned traveler, meticulously packed enough snacks to provision a small army, ensuring Julian would be well-fed. What I neglected, in a monumental oversight, was a simple change of clothes.

Shortly before the roaring engines signaled the race’s commencement, disaster struck. Julian experienced what could only be described as a diaper breach of biblical proportions. Diarrhea cascaded up his back, down his legs, soaking through his shirt, socks, and pants. The VIP suite, moments before a picture of calm anticipation, became the scene of a frantic clean-up operation. For a grueling half-hour, I wrestled with the mess while my husband, bless his heart, scoured every merchandise stand within sprinting distance for children’s pants. To our dismay, nothing, absolutely nothing, was available in Julian’s size. Our salvation ultimately came in the form of an $80, size XL Indianapolis Motor Speedway Christmas sweater—a truly absurd purchase in late spring. We rolled the sleeves five times, cinched the excess fabric behind his neck with a hair tie, and returned our pantless son to the grandstands, clad in what was, functionally, a festive holiday sweater dress.

By then, the race was well underway. The cacophony of engines, the blur of speeding cars, and the electrifying atmosphere enveloped us. When I hoisted Julian up so he could see the colorful machines screaming past, his face erupted into an enormous grin, completely oblivious to his unconventional attire or the recent "poopgate." That day, forever etched in family memory as "Poopgate 2025," became the hilarious tale of how our three-year-old redefined a "blowout at the Indy 500." The moments that make you want to crawl into a hole while they’re happening have a peculiar way of improving with age, morphing into stories that evoke laughter and nostalgia. Someday, that oversized Christmas sweater will finally fit him, and I eagerly anticipate explaining its unique provenance to any future partner he brings home.

Taking a preschooler to Mardi Gras in New Orleans seemed reckless for entirely different reasons: the legendary heaving crowds, the heavy drinking, and the notorious bedlam of Bourbon Street. Conventional wisdom screamed against it. However, having experienced it firsthand, I would now argue that much of Mardi Gras is surprisingly family-friendly. The late-night debauchery, after all, is well past our bedtime. We strategically opted for elevated stands at the Sheraton New Orleans, a setup that offered us a prime, safe perch away from the thickest crowds. The added bonus of Club Lounge access provided not only convenient bathrooms but also a steady supply of snacks, making it easier to manage a child’s needs. The greatest danger, it turned out, was not the beer-fueled mayhem that so many pearl-clutchers had warned us about; it was the enthusiastic, sometimes forceful, pelting of faces with beads from passing floats.

To Julian, every float was a magical toy store on wheels, with krewe members gleefully hurling footballs, stuffed animals, and light-up swords into the eager crowd. He quickly mastered the essential "reach-and-duck" technique: one arm extended, begging for loot, while the other instinctively shielded his head from incoming projectiles. Outside the historic Toulouse Theatre in the French Quarter, rainbow confetti swirled through the air as the street dissolved into one giant, spontaneous Fat Tuesday dance party. Julian, perhaps the only kid there, threw himself into the costumed revelry with uninhibited joy, cutting a rug with strangers who, charmed by his enthusiasm, draped countless strands of beads around his neck. Nobody cared that we had brought a four-year-old; instead, they delighted in his unbridled fun. This experience underscored a profound realization: so much parental anxiety is anticipatory—a knee-jerk "no" that conjures worst-case scenarios before ever giving a place, or more importantly, the child, a chance to prove us wrong.

Alaska in winter put that theory through the ultimate wringer. For Julian’s first spring break, I chose what is arguably the least "spring break-y" destination imaginable, timing our visit to coincide with the 54th annual Iditarod Trail Sled Dog Race’s ceremonial start in downtown Anchorage. We secured a strategic stay at The Wildbirch Hotel, overlooking the race route, which afforded us a front-row spot outside and, crucially, an immediate escape hatch upstairs when the inevitable cold-hungry-bored trifecta hit. We also immersed ourselves in Fur Rondy, Anchorage’s beloved winter festival, where Julian rode snow-covered midway rides and watched costumed Alaskans in inflatable dinosaur suits race alongside actual reindeer in the annual Running of the Reindeer. Everything was going so smoothly, I confess, I grew smug. "Check us out!" I thought. "My hardy Minnesota kid is taking Alaska in winter like a champ."

Then we flew to Fairbanks.

Temperatures plummeted to a brutal -38°F, a chilling reality check. Julian developed a nasty cough and spent a full day zombied out with his iPad, the extreme cold rendering outdoor activities impossible. When he finally felt better, we ventured out to the World Ice Art Championships, a stunning display of frozen artistry. Yet, we spent almost as much time thawing out in the warming tent as we did marveling at the sculptures or whooshing down ice slides. By the time we checked into Sheep Mountain Lodge, a historic collection of rustic cabins nestled in the remote Mat-Su Valley, we were all sick and tired of being sick and tired. The initial glow of our Alaskan adventure had been severely dulled by the relentless cold and illness.

Then, Alaska, in its majestic, unforgiving glory, reminded me why I had dragged us there in the first place. Some tour operators rigidly adhere to age restrictions, refusing to take a four-year-old on a snow machine. But folks up north, hardened by the elements, are often more adventurous and pragmatic. We bundled Julian like a tiny taquito, tucked him securely behind me, and stuck to short, exhilarating loops on a frozen lake. Within minutes, his initial trepidation vanished, replaced by pure delight as he yelled, "Faster, Mama!"

Later that day, Mark Fleenor, the lodge owner and an experienced helicopter pilot, flew us high above the breathtaking Matanuska Glacier. From our aerial perch, we spotted elusive Dall sheep and majestic moose against the pristine white landscape before touching down near an awe-inspiring ice cave. Julian, dwarfed by the towering walls of electric-blue ice, looked tiny and insignificant yet completely mesmerized in that natural cathedral. He picked up a hunk of ancient ice and, with childlike innocence, asked if he could bring it home. "Sure!" Fleenor replied, indulging his curiosity and helping him load it into the helicopter. And just like that, my kid was flying home from a glacier with his own personal iceberg, a tangible piece of this frozen wonder. Alaska had one last laugh when a blizzard stranded us in Anchorage for an extra 48 hours. But it didn’t matter. I would have gladly suffered another month of airport misery for that single, extraordinary day.

These experiences have solidified a fundamental truth: a tantrum abroad is no different than one at home. A sick day is still a sick day. Plans implode. Parents screw up. Kids lose their shit. None of these things automatically means the trip was a mistake or a failure. Earlier this month, Stanley Safaris helped me orchestrate another mother-son trip that sounded ludicrous when detailed aloud: two and a half weeks across South Africa and Madagascar, involving brutal overnight routings through the Netherlands and Ethiopia.

This time, however, I could clearly see the cumulative impact of four-plus years of repeatedly saying "yes" to adventure, even when it seemed daunting. At Tswalu Loapi in the Kalahari, Julian enthusiastically joined game drives, his eyes scanning the horizon for cheetahs and rhinos. He even spent a day at the staff-village school, gaining a unique perspective on local life. Off Madagascar’s northwest coast, at the idyllic Time + Tide Tsara Komba, we hiked through the dense, vibrant Lokobe National Park. Julian, now a confident and curious explorer, tore ahead, utterly enchanted by glossy black lemurs, iridescent poison dart frogs, fist-sized insects, and a Malagasy boa curled on the forest floor like a discarded firehose. He didn’t hesitate. He was game for all of it, his spirit unburdened by fear or apprehension. Watching him disappear deeper into that jungle, I could see the adventurous, resilient kid I had hoped all those allegedly terrible ideas might help me raise.

I’m not suggesting every parent should take a preschooler to New Orleans during Mardi Gras or to Fairbanks in -38°F weather. The point is not to replicate our exact itinerary, but to find your own edge. Stick a toe over it. Book that trip you keep dismissing as "too hard." Maybe it will be a complete disaster, and you’ll swear never again. Or maybe, just maybe, you’ll get your own ice-cave moment, that singular, breathtaking experience that makes every aggravation and every challenge feel immeasurably worth it. Post-travel amnesia has a funny way of preserving the good parts and transforming the worst ones into entertaining stories you’ll eventually laugh about, perhaps even exaggerate slightly.

Ultimately, I want Julian to grow up knowing that difficult doesn’t mean impossible, that a bad day doesn’t mean a bad trip, and that not every experience has to be inherently "great" to be profoundly worth having. I’d rather we collect a few spectacular failures, a trove of wild stories, and a deep well of resilience, than spend our lives wondering what we missed by playing it safe. These journeys, however unconventional, are teaching him to embrace the unknown, adapt to change, and find joy in the unexpected—lessons far more valuable than any perfectly curated vacation could offer.