Traveling the world is fun. Two-year olds are tiring. Here are some ways to make things easier.
Back in 2017, my two-and-a-half year old son and I flew together from NYC to Tel Aviv. We had flown together on our way to New York — where we stopped in Warsaw for coffee at Ministerwysto Kawy , which is seriously awesome — and so I had the time in which to strategize for our return flight.
Before my initial flight with Joshie, I had read a number of blog posts about how to travel with toddlers. A lot of them said things to the effect of “Have low expectations but high hopes” and “Pack lots of diapers” and “Don’t expect to sleep.” Yes, duh, those are all true, but I found a few other hacks/strategies really useful on my return flight.
1. Bungee Cords are your friend. A lot of traveling with a toddler comes down to stuff management. By a stroke of bad luck — the inability of Polish luggage lockers to take any denomination of cash larger than coins — I ended up lugging my toddler, a knapsack, a rolling bag, and a car seat around the Warsaw City Center for the better part of an afternoon. It was rough.

Even if you have more luck than I did, a lot of transition times — getting from your car/taxi to the airport, inside the airport, and so on — will come down to managing all the crap you’ve brought for you and your toddler. (Remember those one-backpack expeditions of your college years? Those are long gone, buddy).

So, in advance of my return flight, I found a two-pack of 4-foot-long bungee cords that I then used to lash all of our stuff — including our two gigantic checked bags — onto a luggage cart for the purpose of navigating the airport. (Side point: LL Bean makes phenomenal duffel bags). It wasn’t easy, but it made the leg of my trip substantially easier. On our return trip stopover, I was simply able to push around an airport cart with every item we owned on it. We looked a bit like a pair of hobos, but it was a fantastic solution.
2. Packing Cubes. I reiterate what I said above: traveling with a toddler comes down to stuff management. During the flight, I must have reached down into bag forty times to grab various, sundry items to fulfill whatever impulse Joshie felt at the time.

Given the cramped nature of sitting in Economy, coupled with the natural accumulation of detritus of used refresher wipes and blankets and empty pretzel bags, reaching down blindly into my bag became a surprisingly arduous task. So it was surprisingly useful to pack two Amazon Basics Packing Cubes: one for me, one for Joshie, each of which contained basically whatever each of us needed, respectively, such that all I had to do was remove the packing cube in order to retrieve whatever I needed at the time. It made my life remarkably easy.
3. Cheap headphones (and Daniel Tiger)

Before our flight, I queued up a thousand episodes of Daniel Tiger on my wife’s iPad. I’m pretty wary of allowing kids too much screen time, but there were times that I simply needed him to tune out for fifteen or twenty minutes at a time. And so an inexpensive pair of wired headphones can go a long way. You really shouldn’t spend much on good headphones, as there is an 80% your kid snaps them in half. Which is exactly what happened on our trip.
4. A Portable Charger and USB Hub
You can file this under General Travel Tips, as well, but I include it here with the specific experience that there were times that I was quite literally running through the airport in Warsaw, chasing after a toddler. But because I was also juggling phone calls, work emails, and Whatsapp messages my battery would drain rather quickly, and I didn’t have the luxury of sitting next to an outlet. (Oh, how I wished I could be one of those unharried travelers who could simply sit with a cup of coffee and swipe away on Instagram.)
One of those lipstick chargers usually has enough juice for one full charge. (I’ve also used them for ultra-marathons, though you’ll need two for a 50K).
I mention the USB hub because, once you do eventually get the time to sit down and literally recharge, it’s helpful to be able to juice your phone, tablet, and porta-charger all at the same time.
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I intend to keep this list updated as I travel more, and, I hope, discover more ways to make traveling — with or without kids — fun and enjoyable. If I missed anything, feel free to ping me on Twitter. I hope this was helpful to those of you who are also considering taking your kid(s) on flights across the globe. It’s exhausting and exasperating, but it can also be manageable. Here’s to the crazy ones. We may as well be prepared.