Flying with a Toddler: Our Honest Guide to Surviving Long-Haul Airplane Journeys

After receiving invaluable insights and encouragement from fellow parents about navigating air travel with a toddler, we embarked on a multi-leg journey. Now, we’re thrilled to share our comprehensive recap of what truly worked wonders and, crucially, what proved to be a challenging misstep. Spoiler alert: Lollipops were a godsend, while the infamous red-eye flight was anything but.

Our Epic Six-Flight Adventure: Setting the Stage for Toddler Travel

Our recent family vacation involved a significant amount of air travel—a total of six flights. The outbound journey included two flights to Portland, Oregon, with a layover in Chicago. From Portland, we enjoyed a direct, six-hour flight to Maui, Hawaii. The return trip presented an even greater challenge, comprising three flights back to Richmond, Virginia, with layovers in Seattle and Chicago. The segments between the West Coast and Hawaii were the longest, each stretching approximately six hours. Given that our daughter, Clara, is still under two, we opted not to purchase a separate seat for her. Our reasoning was simple: she finds the most comfort in our laps, and we anticipated potential protests if we tried to seat her elsewhere. We understood from the outset that this trip would demand immense patience and strategic planning. Our primary mission was clear: keep Clara happy and relatively calm at all costs, while actively encouraging sleep whenever possible. Oh, and amidst all this, we hoped to enjoy the journey ourselves as best we could.

Some flights surpassed our expectations, such as the delightful journey to Maui where we were fortunate enough to have an empty seat beside us—a rare luxury when flying with a little one! Others, however, veered into truly nightmarish territory. For these flights, our strategically packed “monkey backpack” became our ultimate survival kit, brimming with items designed to keep Clara engaged and entertained. Here’s a detailed look at the tools and tactics that proved most effective.

The Toddler Travel Survival Kit: What Worked Wonders on Our Flights

1. Crayons and Coloring Books: Simple Yet Powerful Distractions

• Engaging Activities: From vibrant coloring sessions to jointly identifying colors and simply the satisfying act of pulling crayons in and out of their boxes, these classic art supplies were undeniably our biggest hit. They provided sustained engagement, tapping into Clara’s natural curiosity and fine motor skills.

2. The Essential Snack Strategy: Fueling Happiness and Comfort

• Favorite Treats: We heavily relied on familiar favorites like Goldfish crackers and Teddy Grahams. A crucial piece of advice we received, and one we wholeheartedly endorse, is that in the rush to keep kids occupied, parents can sometimes overlook the simplest need: hunger. Being well-stocked with a variety of snacks, alongside a trusty water cup, was paramount. Clara also developed a fondness for the crushed ice served by the flight attendants during drink service and enjoyed playfully “experimenting” by transferring snacks into different cups, much like a tiny mad scientist.
• Beyond Hunger: Snacks aren’t just for hunger; they offer a wonderful distraction, can help with ear pressure during ascent and descent (especially chewy ones), and provide a sense of comfort in a new environment.

3. Lollipops: A Sweet Solution for Ear Pressure and Calm

• A Game-Changer for Ears: Someone cleverly suggested lollipops as an ingenious way to encourage children to swallow repeatedly during take-off and landing, thereby alleviating ear discomfort. Clara, bless her heart, made a substantial dent in our supply of Dum-Dums—not just during the crucial ascent and descent, but before, during, and after the flights! Since our overarching goal was to maintain her happiness and ensure minimal disturbance to fellow passengers, we embraced their effectiveness.
• Unexpected Bonus: While we may now have a budding lollipop enthusiast on our hands, their efficacy in the air was undeniable: absolutely no complaints during take-off or landing. Not a single ear tug or whine! An added discovery was that the rhythmic sucking motion seemed to induce a gentle sleepiness, a welcome bonus on those long flights.

4. Engaging with the Airplane Environment: Curiosity as Entertainment

• People-Watching and Interactions: Clara genuinely loved simply observing her surroundings on the plane. She’d stand up, excitedly greet passengers with “Hi people!” or “Hi lady!” We jokingly dubbed her the “mayor of the plane” by the time we disembarked, given her knack for charming so many people. On one particular leg, she grew so comfortable she nearly crawled into our seatmate’s lap (thankfully, he was a good sport!).
• Window Views: And, of course, gazing out the window at the clouds, the miniature landscapes below, and other planes was always a captivating hit. Pointing out different shapes and colors provided simple, yet effective, entertainment.

5. Airport Layover Adventures: Turning Waiting Time into Playtime

• Burning Energy: Beyond the flights themselves, our itinerary included a couple of three-hour layovers. Keeping Clara occupied and content during these periods was equally important. We spent most of this time walking around the airport, allowing her to stretch her legs and expend some energy—a strategy we hoped would lead to sleep on the subsequent flight (alas, often in vain).
• The Allure of Moving Walkways: Predictably, she was most drawn to the moving walkways, which she delightedly called “escalators.” Airports, we discovered, are far more interesting than we remembered. O’Hare boasted a massive dinosaur skeleton, Sea-Tac featured intriguing sculptures, and PDX (Portland) had a toy store that provided a welcome distraction for quite a while. These unexpected gems were a true blessing.

6. Committing to Local Time: Our Jet Lag Busting Strategy

• Immediate Adjustment: We made a conscious decision to immediately commit to the local time zone upon arrival at each destination, and this strategy proved incredibly successful for our family. We reasoned that Clara’s internal clock was already disrupted by the flights, so we might as well seize the opportunity to reset it with each time zone change.
• A Practical Example: When we landed in Portland, it was actually her bedtime in EST. Having woken two hours early that day and foregone any naps on the flights, she was utterly exhausted by the time we checked into our hotel. We put her down for a nap, but only for an hour and a half. After waking her, we headed out for dinner (and dessert!) before putting her to bed around 8:30 pm PST for the night. This bold move paid off beautifully: she was perfectly on schedule for the next two days, with no dreaded 5:30 am wake-ups—a true victory! We applied the same principle in Hawaii, keeping her awake until 8 pm HST on the first night and then maintaining her regular 1 pm nap schedule each day thereafter. This approach significantly helped us establish normal wake-up and nap times throughout our trip.

Navigating Turbulence: What Didn’t Work So Well for Our Toddler Travel

Now, for the less successful aspects of our journey. Sigh…

1. The Screen Time Dilemma: Videos Fell Flat

• Home vs. Plane: While Clara adores videos at home, she showed surprisingly little interest in them on the plane. They offered some momentary distraction, but her primary frustration stemmed from the inability to access her favorite KidsTV123 videos on YouTube, a casualty of the Wi-Fi-free airplane environment. Pre-downloaded content might have helped, but even then, the novelty of the plane often outweighed screen allure.

2. The Elusive Airplane Sleep: Dreams Dashed

• Reality Check: Our hopeful dreams of long flights filled with a slumbering toddler curled comfortably in our laps were swiftly shattered. Clara has always been an excellent sleeper… in her crib… at night. The fact that she rarely sleeps well in her car seat or stroller should have been a clue, but we clung to the hope that she would eventually “crash” from sheer exhaustion.
• A Brief Respite: On the way to Portland, she literally fell asleep for precisely thirty seconds the moment our wheels touched down at PDX. Oh, the irony! That fleeting moment of sleep was all we got during the entire nine hours of travel, though we were grateful she remained generally happy. The spare seat on the flight to Maui offered some relief, allowing her to nap for about an hour during that six-hour journey. It wasn’t much, but at that point, we’d take any sleep we could get.

3. The Red-Eye Revelation: A Cautionary Tale for Parents

• A Known Risk: We knew, deep down, that booking an overnight red-eye flight was likely a poor decision. However, avoiding it would have meant an additional overnight stay on the West Coast on our way home, which seemed equally daunting. Banking on Clara’s reputation as a sound night sleeper, we optimistically believed she’d be knocked out cold for the duration, allowing us to follow suit.
• The Unfolding Nightmare: Our flight departed Kahului at 10 pm HST (which was 3 am EST, though Clara had adjusted well to Maui time, so it truly felt like 10 pm to her). She hadn’t napped much that day, and we ensured she ran around the airport right up until boarding, at which point she finally started to look sleepy. Perfect, right? Wrong. Utterly wrong. She simply could not get comfortable on the plane. It was a full flight—hooray!—(that’s sarcasm, for the record), and despite our desperate attempts to soothe her in our arms, it was futile. She managed a mere forty-five minutes of sleep before waking in a terrifying, screaming night terror. Yes, people absolutely loved us.
• Flight Attendant Angels: We are eternally grateful to the incredibly cool flight attendants (a special shout-out to Rebekah, who quite literally saved our sanity!). They allowed us to relocate to the back of the plane, where Clara found solace by snacking, enjoying gentle rocking, and generally maintaining a calmer demeanor. This heroic act allowed the rest of the plane to sleep soundly throughout the flight… while we remained wide awake… all… night… long.
• A Glimmer of Hope: Thankfully, she graced us with an hour-long nap on the subsequent flight between Seattle and Chicago. Hey, at this point, we’d gratefully accept any sleep. The accompanying photo perfectly captures Sherry’s “I’m tired” face. By Friday morning, we hadn’t slept since Wednesday night, having endured a sleepless Thursday night red-eye.

The sheer disaster of the red-eye flight completely derailed the rest of our travel day. All three of us were utterly exhausted and more than a little grumpy. Many of the engaging activities that had worked so well on the outbound flights simply held no interest anymore; even lollipops couldn’t capture her attention for more than a few seconds. This, coupled with frustrating delays both into and out of Chicago, made for a day we were all desperate to conclude. You can’t tell from this photo, but it was snowing outside. We were definitely no longer in Hawaii.

We finally touched down in Richmond around 9:30 pm EST—approximately 19 hours after we departed Hawaii and two hours behind schedule. In total, Clara probably managed about three hours of sleep across that entire 19-hour journey, much of which was overnight. Sherry and I likely each snatched about half of that amount in terms of catching any Zzzs. But at that moment, all that mattered was that it was finally OVER. Even better, we could at long last go to bed. And boy, did we. After not sleeping at all on Thursday night (remember, our last actual full night’s sleep was Wednesday night), we all slept until 1 pm on Saturday. Yes, that’s fifteen glorious, solid hours. And yes, it felt absolutely awesome. Of course, we gently shifted Clara’s naps and night sleep back to her normal times, and she seems to be back on schedule, with the delightful bonus of sleeping in an extra hour or two in the morning (which, crucially, doesn’t affect her bedtime or her 1 pm nap, so we’re ecstatic!). We’re confident she’ll naturally revert to her old schedule over time.

Key Takeaways: Why We’re Swearing Off Red-Eyes with a Toddler

I think it’s safe to definitively say that we will not be taking any more red-eye flights with a toddler. Ever again. It was a significant miscalculation on our part. We even heard from not one, but two different flight attendants that young children rarely sleep on red-eyes, even those who are excellent night sleepers at home. They emphatically stated they would never take a red-eye with their own kids. This invaluable insight, unfortunately, came a little late for us! We hope this shared experience helps other parents considering such a journey. The intense stress of trying to keep your child quiet while the cabin lights are out and everyone else is attempting to sleep—all while you are incredibly tired yourself—is simply not for the faint of heart. Flexibility, patience, and realistic expectations are vital when flying with young children.

Share Your Stories and Tips: What Are Your Best Toddler Travel Hacks?

Does anyone else have a travel story with kids or a toddler that they’d love to share? Or perhaps you have additional tips we might consider when Clara is a bit older and we are foolish enough to attempt something similar again? We’re always eager to learn from fellow parent travelers!