After receiving so many helpful tips from readers about flying with a toddler, we wanted to share a concise recap of what worked (lollipops!) and what didn’t (two words: red eye).
We logged a lot of time in the air: six flights in total. Two on the way to Portland (with a layover in Chicago), one direct from Portland to Maui, and three on the return to Richmond (layovers in Seattle and Chicago). The West Coast–Hawaii legs were the longest at six hours each. Since Clara is under two, we didn’t buy a seat for her — she’s most comfortable in our laps, and we figured buying a seat might not prevent a loud scene. Our plan was simple: keep Clara content (and as quiet as possible), encourage sleep whenever we could, and try to enjoy the trip.
Some flights went surprisingly well (we even had an empty seat next to us heading to Maui), while others were rough — especially the red-eye. One of our carry-ons was Clara’s monkey backpack, packed with items to keep her busy. Here’s what proved useful:
- Crayons and coloring books. Simple and portable, these were a huge hit. Coloring together, naming colors, and taking crayons in and out of the box kept her entertained for long stretches.
- Snacks. Goldfish crackers and Teddy Grahams saved the day more than once. It’s easy to overlook hunger when you’re focused on activities, so having familiar snacks and a water cup on hand matters. Clara also loved crushed ice from drink service and enjoyed transferring snacks between cups like a little experiment.
- Lollipops. A reader tip that worked brilliantly. Sucking during takeoff and landing helped prevent ear pain and surprisingly soothed Clara — she napped a little while sucking. We did go through a lot of dum-dums, but they prevented any ear-related tears and kept her calm.
- Talking about the plane. Clara loved exploring and greeting people. She stood up to wave and say “Hi,” chatted with nearby passengers, and peered out the window. Her friendliness made the flight more pleasant for everyone and earned her plenty of smiles.
- Moving walkways and airport discoveries. Long layovers meant we needed to stretch her legs. Walking the terminals, exploring moving walkways (she called them “escalators”), and visiting an airport toy store helped burn energy. Airports had unexpected distractions — displays and sculptures that captured her attention and kept her engaged between flights.
- Committing to local time. We decided to immediately adopt the local timezone at each destination. When we arrived in Portland it was bedtime back home, but Clara was already tired from the day, so we gave her a short nap, then woke her for dinner and put her to bed at a reasonable local hour. We followed the same approach in Hawaii, keeping her awake until the evening and then resuming local nap and bedtime routines. That helped her adjust quickly and kept mornings and naps on track for the rest of the trip.
Now for what didn’t work so well:
- Videos. Although Clara loves videos at home, she wasn’t interested on the plane. Without Wi-Fi and her usual YouTube favorites, screens didn’t hold her attention the way we’d hoped.
- Sleep in transit. We’d hoped for long lapside naps but learned that Clara rarely sleeps well in car seats or strollers, and that carried over to plane seats. On the first travel day she slept for exactly thirty seconds once we landed — a cruel joke. We did manage about an hour on one long flight, but overall in-flight sleep was limited.
- The red-eye flight. Booking an overnight flight proved to be a mistake. We thought Clara, a solid night sleeper at home, might sleep through it, but a full cabin and an uncomfortable setting prevented that. She managed about 45 minutes of sleep before waking upset. Flight attendants were wonderful and helped us move to the back of the plane so she could be rocked and fed without disturbing others, but we ended up sleepless all night. We later learned from multiple attendants that kids rarely sleep on red-eyes, even good sleepers — something to keep in mind.
The red-eye disrupted the rest of the day. We were all exhausted and more short-tempered, and many tricks that had worked earlier in the trip no longer held her interest. Flight delays added to the fatigue. We finally landed in Richmond around 9:30pm EST, roughly 19 hours after leaving Hawaii. Clara likely slept about three hours total during that stretch, so the adults only managed fragments of rest. The important thing: we made it, and the trip ended.
Once home we caught up on sleep — a glorious long nap for all of us — and gently returned Clara to her usual nap and bedtime schedule. She took an extra morning hour or two for a few days, but otherwise normalized quickly. Lesson learned: no more red-eyes with a toddler. Hearing flight attendants confirm kids rarely sleep on overnight flights validated our experience — the strain of keeping a child quiet while everyone else sleeps is tough and not worth it.
Have a travel-with-kids story to share or extra tips we should try next time? We’d love to hear your experiences and suggestions.