Traveling with and for kids

2026-03-07

We are taking our third flying (it is either our third or fourth) trip with our two kids just now, and I must say that traveling with two kids seems different than traveling with one. It is similar to parenting two kids vs one, there is no switching and getting a break, not a lot of down time except at night (or times like right now when everyone is taking a nap but me). And our plan and activities have changed a ton obviously.

But the first thing I want to say is that our first flying trip with two kids was pretty terrible, and it was also to Hawaii. It wasn’t as terrible as my mom having a stroke (sorry joke for Sneha), but it was terrible. Our youngest was still around 4 months I think, he got up twice a night every night. This was hard because we were in an Airbnb with a crying infant at 2AM and 5AM every day, Sneha had to pump milk multiple times a day, we did a ton of bottle cleaning, feedings, and such. We also had to cook food for ourselves, we had some family help and that was great, but we also had to clean up normal non baby related stuff. We were stuck at the Airbnb often. And for those times that we weren’t stuck at the Airbnb we wanted to give our older kid a good time so we would pack up and go to the beach where he would play in the sand and we would watch both kids and try to make sure no one got swept away into the ocean. And in hindsight I wouldn’t have gone on that trip, but alas I am not given the gift of foresight so I would call that trip a learning experience.

That trip scarred me a bit and I was gunshy around flying trips. With our oldest we flew much more frequently when he was very young and were more adventurous. Our second flying trip with both kids was to Chicago which was marginally better, I think the kids were 1 years and 3.5 years, approximately. We stayed with a lovely family but every outing was hard.

And that all leads up to this trip which has gone much better than the first, we are back in Hawaii. The kids are 1.5 years and 4 (almost 4) years old now. The oldest is kind of independent, he is afraid of the elevator and the water sometimes. The youngest is still in diapers but at least we have no more bottles and no more pumping. And there is some shared pool of activities both kids can do, they can both hang out near the pool, they can both visit a goat farm. Some parts are still mixed bags. The flight was still hard, I carried our youngest for 5 hours straight and my back hurt, I assume that will be the same on the way back. Carrying diapers is not the most fun. Our kids dont always eat the same things so sometimes we have to get a bunch of different food to satisfy them. And as I mentioned up top there is not a lot of downtime for parents. But vacations have come a long way since one year ago.

And finally the story that I wanted to share, two days ago I was hanging out with our youngest while Sneha and the oldest were trying to sleep. And our youngest is awake and I am trying to entertain him but he keeps crying. So I take him in the car and drive him to the grocery story. While driving he also falls asleep in the car, so I park in a shady spot and watch a youtube video. And that is how I spent an hour of my day in Hawaii, I kept the car running for the youngest to stay cool, my wife and oldest napped back in the hotel, and I chilled in the car for an hour. And honestly I was just happy that our youngest got in a nap, he was so tired and didn’t nap well previously. Traveling without kids I would not have been super happy sitting in a parked car in Hawaii for an hour, it is just kind of a waste of time when I could have been doing anything else, but with two kids I am happy when they are happy and I am happy when they are well fed and well rested.

-Gary