Guest Q&A: 100 flights before kindergarten
What a frequent flyer mom recommends | 5 min read
My blog on baby’s first flight is now a top Google search result for ‘baby’s first flight’, and I think I know why:
Flying with a baby is stressful. It’s one of those experiences people dread before they even book the ticket.
So, I called in an expert for her tips on flying and traveling. A close friend of mine (we’ll call her ‘Frequent Flyer Mom’) has two boys and flew with them 100 times before her oldest turned 5 years — international flights, red-eyes, she’d done it all. And somehow, she keeps going for it.
She shared what works, what doesn’t, what she always packs (and it’s not diapers), and what she wishes someone told her.
Here’s our conversation:
✈️ Q: What’s your favorite ‘travel win’ story? Or a time when things went really well.
Three come to mind.
The first is figuring out when kids can actually entertain themselves. We were at a beach in Belize and didn’t get a babysitter. The water was shallow and calm, the kids had floaties, and there were enough people around that we could relax without watching them every second. That’s the kind of situation where everyone gets to have a good time.
The second, is when my husband and I got a couples massage in Japan. We asked the hotel if the kids could be in the room with us, and they said yes. So the boys just sat in the corner and watched TV while we got massages. Everybody was happy.
We also try to book a private tour instead of a group one when we can, even if it costs more. We did a day trip to see the ruins in Guatemala and having a private guide meant we could go at our own pace instead of worrying about holding up a bus full of strangers. It’s worth it for everyone’s sanity — including others on the tour.
✈️ Q: What’s the worst thing that’s ever happened on a flight?
Honestly, one of our shortest flights was one of the worst. My son was overtired and screamed almost the entire time. We got a lot of dirty looks from other passengers, and in the moment there wasn’t much we could do.
What we’ve learned since then is timing naps before red-eyes. We used to try keeping them up until midnight, thinking they’d definitely fall asleep on the plan. That backfired every time.
Now, we put them to bed at 8 or 9 PM, like normal, let them get a real two-hour nap, and then wake them up to leave for the airport. They’re not going to fall asleep again until 2 or 3 AM anyway because of the noise and new environment, so that first nap matters a lot more than people think.
We also started bringing the car seat on the plane. Not for safety, but because our kids fall asleep so much easier in their car seat than in our laps or lying across seats. It’s more to carry, but it’s worth it.
✈️ Q: What’s your packing strategy?
We stopped bringing toys altogether. When we land, we'll go to a thrift store and buy some secondhand toys. The kids think it's all new and we just leave everything behind at the hotel so we don't have to haul it back home. Kids also don't need much and can happily entertain themselves with Tupperware or unbreakable kitchen stuff in an AirBnB. For the flight, we bring a couple small things. Like lightweight 3D puzzles, pop it fidget spinners, and others that pack easily.
The stroller is the one everyone assumes you need and we’ve learned to think that one through depending on the trip. If you’re renting a car and driving everywhere, you probably don’t need one. If you’re navigating a city like NYC with a lot of subways and stairs, a stroller can honestly be more of a hassle than help. You end up hunting for stations that have elevators.
If you’re staying somewhere for a longer stretch, it’s often cheaper to just buy diapers or even a cheap pack n play once you arrive,. That saves you from checking an extra bag or lugging it through the airport.
✈️ Q: Any tips for babysitters or childcare while traveling?
We almost always try to get a sitter for at least 1 night of the trip. There are just some things you can't do with kids along. We’ve found sitters through AirBnB hosts (ask if they know someone local, it tends to be cheaper) or through a nanny agency as a backup (more expensive, but usually vetted and reliable).
One thing that’s worked well: If it’s a new sitter, we’ll have them come a 1-2 days before we need them and spend time with the family — walk around town with us or grab lunch together — before we ever leave them alone with the kids. That gives us a chance to see if it isn’t a fit and adjust our plans (vs. learning the hard way on the night we really need the break).
And no matter how much we like the sitter, we don’t have them take the kids out of the hotel or AirBnB. They just stay put together.
✈️ Q: Anything you always pack that people might not think of?
Infant Tylenol, Motrin, or Benadryl travel with us every single time. When you're traveling abroad, it's surprisingly hard to find. One of our kids had a bad allergic reaction on a short flight once, and it got serious enough that they made an announcement on the plane asking if anyone had infant Benadryl on board. We also look up the nearest urgent care or hospital wherever we’re staying, just for peace of mind. We’ve actually needed it. One of my sons got stung by a jellyfish on a trip. Everything else on a trip you can figure out or adjust as you go, but health and safety is the one thing you want a plan for before you need it.
✈️ Q: If you could give one piece of advice to someone traveling with a baby for the first time, what would it be?
Adjust your expectations. It's not going to be the same as traveling without kids, and it's not going to be relaxing. But it can still be a genuinely fun adventure if you go in expecting that. If the idea of that trade-off stresses you out more than it excites you, that’s OK too; not every trip has to happen right now.
Mostly though, you just have to roll with it.
Thanks so much to my friend for sharing so much of her frequent flyer wisdom. If you’re getting ready for your first flight with a baby, you can also check out my original tips post.
To learn more about what helped me de-stress firsts with my first baby (sleep, feeding, and more), check out the link below:
