If you’re here, chances are you’re feeling a little overwhelmed at the idea of traveling with your kids—and you’re not alone. Whether it’s your first trip as a new parent or your tenth attempt at keeping a toddler entertained mid-flight, family travel comes with a lot of moving parts.
I get it. I’ve been there—with twins. I started traveling with my boys when they were just four months old. By six months, we took our first international trip. By one, they had been to Asia. And now, at just seven years old, they’ve been on more than 50 trips and visited 10 different countries.
So yeah, I’ve had blowouts in airport bathrooms, meltdowns mid-boarding, and tried to juggle sippy cups, sound machines, and snack bags through customs. And yet—I still choose travel, every time.
Because here’s the thing: the struggles you face on the road? You’d be dealing with many of them at home, too. The tantrums, the potty accidents, the logistics of feeding and entertaining small humans—they don’t magically disappear just because you’re not traveling. So I’d rather be navigating those same challenges on a beach in the Caribbean, soaking up sunshine between snack breaks, than sitting at home watching Bluey for the 100th time.
In this post, I’m breaking down the biggest challenges of traveling with kids—from babies to big kids—and more importantly, how I’ve learned to ease those struggles along the way. Let’s dive in.
The Biggest Challenges of Traveling With Babies
Traveling with babies might be the most intimidating stage to start with, but it’s also the one that taught me the most. Between gear overload, communication struggles, and constant diaper changes, those early trips were a masterclass in adapting on the fly.
So. Much. Stuff.
When we first started traveling with our twins at four months old, we brought everything—our full-size double stroller, car seats, travel bags, you name it. The real breaking point? Trying to fold a bulky stroller at the gate, while holding a baby, juggling a carry-on, and trying not to drop anything valuable.
The fix? I stopped traveling with our large stroller. When I had another adult, we each babywore one twin. When I was solo, I babywore one and used a GB Pockit stroller for the other. It folds small enough to go in the overhead bin. Total game-changer.
Also, make sure to check out the TSA’s guidelines for traveling with children so you know what to expect during airport security.
The Blowout Epidemic
For some reason, my kids always had a blowout at the airport. Not once or twice—several times. I created what I now call my “blowout bag”: a gallon Ziploc with two diapers, a travel pack of wipes, a change of clothes, and a doggy training pad. It made cleanup easy and contained the mess every time.
The Communication Struggle
Babies don’t talk. At 30,000 feet, trying to decode cries while everyone’s watching is a pressure cooker. Eventually, I learned to manage my mindset. I reminded myself: these strangers don’t matter. My baby deserves to be there just as much as anyone else. Want help staying grounded? Grab my Mindset Checklist.
Are Babies Even Welcome?
Not every destination or restaurant is designed with babies in mind. I started calling ahead to ask about accommodations. I also brought my own gear—like a portable travel high chair—so I always had a clean, safe place for them to eat, no matter where we were.
The Biggest Hurdles to Traveling With Toddlers
Toddlers are mobile, opinionated, and unpredictable. But traveling with them can still be fun, with the right strategy.
Toddler Logic Is… Unpredictable
What worked yesterday won’t work today. One day, bananas are their favorite snack. The next? You’d think I offered them poison. This age is all about big emotions and changing preferences, and learning to roll with it became a crucial part of our travel strategy. I learned to prep what I could and mentally prepare to go with the flow. Need packing help? Here’s my list of toddler travel essentials.
They Want to Carry It… Until They Don’t
My twins were determined to be big boys, which meant they suddenly refused to ride in a stroller. Enter: the wagon. It gave them a sense of independence, and I still had a way to keep everyone moving without chasing two unpredictable toddlers through the airport.
Our rule? You’re either riding in it or helping pull it. That simple guideline gave them a little autonomy without turning travel into a power struggle. Pro tip: the wagon also lets you carry their stuff, so it’s a win-win for everyone.
Potty Training in Public
We were deplaning during a layover when one of my kids had an accident right on the jetbridge. That was my wake-up call—I dropped the “no pull-ups” rule. While traveling, I made peace with using pull-ups. Less pressure, fewer emergencies, and a lot less stress for all of us. We’d change into undies once we arrived and got settled at the hotel.
Nap or Nightmare
No nap = full meltdown mode. While I didn’t schedule our whole day around naps, I always left room for downtime. We’d hit the best attractions first thing in the morning while they were fresh, and schedule chill time in the afternoon.
And when naps needed to happen on the go, I made sure their stroller or wagon was nap-friendly. A familiar blanket helped a lot. Some parents also swear by a clip-on stroller fan or a portable sound machine to help create a cozy nap environment wherever you are.
And when we weren’t sure about sleep setups—especially when we moved past the crib stage—I found that bringing one of these portable travel beds gave us peace of mind and better sleep for everyone.
If you’re flying, here’s how to get a baby to sleep on a plane. For more on keeping your cool in the air, check out this guide to flying with toddlers.
The Hardest Struggles of Traveling With Older Kids
As kids grow, the challenges change. Now it’s not diapers—it’s logistics and price tags.
Budget Hits Different
Once your kids age out of “free” anything, travel costs go way up. Airfare, excursions, dining—it adds up fast. I remember the first time I saw the price of four full-priced tickets on a long-haul flight and had to sit down.
To make it work:
- We use travel deals and reward points when booking flights
- I look for accommodation with kitchens so we can cook a few meals ourselves
- We prioritize local experiences or free attractions (parks, street markets, cultural festivals) over big-ticket tours
- I also ask about family bundles or kid discounts at every activity—we’ve saved hundreds just by asking
The School & Sports Schedule Juggle
Gone are the days of spontaneous weekday getaways. With school schedules, sports practice, and extracurriculars, our travel windows are tighter. I map out the school year ahead of time and highlight potential travel slots—long weekends, spring break, even teacher workdays.
One year, we took advantage of a random two-day school closure and turned it into a 4-day trip to Puerto Rico. I emailed the teachers in advance and packed some homework. It worked out perfectly—and the kids still talk about that trip.
Conclusion
Traveling with kids is full of surprises, and not all of them are fun. But here’s what I know: most of the hard stuff exists whether you’re on the road or not. So why not face those moments somewhere beautiful, somewhere new, and somewhere you actually want to be?
With a bit of prep, a lot of patience, and a good sense of humor, you can make travel with kids not only doable—but enjoyable.
What’s been your biggest challenge when traveling with your kids? Drop it in the comments—I’d love to swap stories and solutions.
