A few weeks ago, we went to Hawaii. It was an amazing trip, but there was one big hurdle before we got there: the airplane trip. Ten hours, one very short layover. With an active 3-year-old.

Frankly, I was terrified. Between chronic illness and said 3-year-old, I am rarely on top of anything, but terror spurred me to be on top of this plane ride. Military skirmishes have happened with less planning than I put into the contents of that carry-on bag. So thought I’d share the details for anyone out there facing a similar situation:

The bag:

My daughter is obsessed with the Disney Princess rolling suitcases from Heys Luggage. My husband and I have certain feelings about the “princess industrial complex” that pretty much guarantee the Disney suitcase is never going to happen, but I wanted her to feel that the eventual choice was special. I looked into Melissa and Doug’s Trunki, a ride-on suitcase that’s popular with the tot set, but many owners grumbled about design flaws like wheels that pop off and a tendency to tip over. Not what you need when you’re rushing to your gate! Any well-made kid-sized rolling suitcase was surprisingly pricey, plus Mom and Dad would end up carrying it eventually and very few have shoulder straps for grownups. In the end I did what I usually do, and headed over to eBay. Found a kid-sized duffel bag with ballet slippers on it to please our budding ballerina — $12 shipped, and we were good to go.

The contents:

Next issue — what to put in it?

  • Snacks. I grabbed any pre-wrapped special treats that we had in the cupboards (freeze-dried fruit, fruit roll-ups, lollipops) and added snack-sized ziploc bags of goldfish crackers (avoid real crackers; they turn to crumbs), almonds, dried cherries, and the like. (Brought string cheese too, but that always turns to warm mush before we get around to eating it. Someday I’ll remember that.)
  • Extra clothesOur girl rarely needs changes of clothes in normal daily life, but something about plane trips seems to guarantee leaky diapers and monumental beverage spills. Bring more extra clothes (tops and bottoms) than you think you could possibly need.
  • Amusements. Bring at least one old favorite that you know will fill some time, plus a handful of new diversions that, if nothing else, will dazzle with their newness. Try wrapping them in gift wrap or tissue paper to make the event feel extra special. Each time your child starts to grow bored and restless, you can pull out a new gift. We packed a set of small foam toys, a pop-up book (turned out to be a smidgen old for our girl, but pop-ups are a great diversion where storybooks might be hard to follow), a small book of sticker paper dolls, and Dollar Store favorites like a plastic Slinky, crayons and paper and a pre-inked stamper, sheets of stickers, and a handful of colorful Band-Aids (Band-Aids are oddly mesmerizing to toddlers).
  • Kid-sized headphones. If you’re going to watch videos on your own device or in-flight entertainment, a comfortable pair of kid-sized headphones is a must. Ours aren’t cute, but they work well. (I once fell for some travel-blogger favorites that look like tigers. They were adorable, but they broke literally the moment we took them out of the package.)
  • Comfort item(s). If your child has a favorite blankie, stuffed animal, etc., you should bring it on the plane. Anything familiar that makes your little one feel safe in strange surroundings is an obvious plus. But be sure to check, double-check, and triple-check that you have this item with you at all times. Losing your child’s beloved mid-trip is a sure recipe for misery.

Other bags / the milk crisis:

That little carry-on wasn’t everything, of course. (How does adding one kid to the trip always seem to triple your luggage contents??!?) We also carried an insulated lunch tote with her milk and sippy cups. And the grown-up luggage had Pull-ups and wipes and diaper disposal bags (as with clothes, calculate how many you think you’ll need and then double it just to be safe!), extra extra clothes, extra grown-up clothes (turned out to need them; see: monumental spills), a travel pillow that’s another comforting friend from home, and the iPad. I also added Children’s Tylenol to my container of “just in case” medications and a small hand sanitizer to my baggie of carry-on liquids.

We’ve been through security with her cooler bag over 15 times, and Dulles was the first time they gave us grief over bringing milk through Security. The TSA agent kept repeating that the milk exception was for “infants and babies only.” They dumped all our milk and re-xrayed the bag, thereby neutralizing the latest pressing threat to airline safety in America. Also leaving us without any milk and facing a 5-hour flight, and if you’ve never shopped for milk at an airport, let me assure you that it’s surprisingly difficult to find. Hot tip: Starbucks sells “kids’ milk” at the counter. Don’t be put off by the flavored milk in the case; ask the barista for regular milk in a cup. It has been a lifesaver in every airport we’ve been through, and they came through for us again at Dulles. (It turns out the stewardesses had cartons of milk available on our plane as well. But that is not always true, and you don’t want to find that out after you’re stuck on a plane with a grumpy toddler who needs milk to fall asleep!)

Speaking of the iPad:

When we first had a baby, an acquaintance described his then-newfangled iPad as “the ultimate toddler pacification device.” He was not wrong. Fellow travelers have our own iPad to thank for their peace and quiet on our past plane, boat, and train trips. We downloaded a few favorite Pocoyo and Hopla videos and have a folder full of toddler apps. We generally stick with free apps or free previews — just search Google or the App Store for toddler or preschool apps and look for the free ones. But Elmo’s ABCs and Monkey Preschool Lunchbox are two that are absolutely worth their retail price.

And the big question … how did it turn out?

Brilliantly! She slept for maybe 2 hours of the 10-hour flight, but her bag kept her well fed and well entertained for the rest of the time. We definitely ran into spills and Pull-up leaks (hence my stress on extra changes of clothes), and airline bathrooms can be loud and scary for kids who are still potty training. But I’m pretty sure Mom and Dad were complaining worse than Kiddo by the time we got to Honolulu. Kids aren’t as cramped as adults in airplane seats, and they have no experience with petty grumbles like lack of food and creeping airline fees. As long as you plan ahead to keep your toddler comfortable, entertained, reasonably well fed, and psychologically secure, plane travel can actually be a thrilling part of your child’s trip.

What’s your best advice for keeping littles ones happy on airplanes? What do you pack in your carry-on?