I’ve gone a few rounds with The Deal Mommy on the worst age to fly and at this point unless she declares an age above of seven to be the worst, we’ll just have to agree to disagree in perpetuity. At this point I’ve flown with the same number of three year olds and 50% more toddlers than Dia, so I’m gonna pull rank. 🙂 Kidding aside, it had been awhile since we flew longhaul with a toddler. Our recent trip reminded me what compromises are made when traveling with a toddler. So in typical asthejoeflies fashion I decided to stream of consciousness some of my thoughts about what makes traveling with a toddler so tough and what we did to make our trip to Hawaii as smooth as possible.

Hopefully I’ll write up some thoughts on Hawaii later, but just in case: it’s awesome, Hilton Hawaiian Village Waikiki Beach Resort was great and Aulani: a Disney Resort & Spa was spectacular. I recorded a short podcast about it for Patreon supporters of the Saverocity Observation Deck in case you’re interested. Anyway, let’s get to talking about traveling with a toddler and what we do to maximize the experience.

Our Hawaii trip and family size

Some notes on our trip and our family’s current makeup since this might be the last time we ever fly with a lap infant (!). We traveled as a family of five, myself, my wife, our 6 year old daughter, 4 year old son, and 19 month daughter. We flew to Detroit and overnighted there before flying Delta One DTW-HNL. 

Once on Oahu, we spent five nights at the Hilton Hawaiian Village Waikiki Beach Resort and then five nights at Aulani, Disney’s resort in Hawaii. We were with a bunch of other families at the Hilton and my parents joined us in Aulani. We didn’t rent a car in Waikiki but did for the second half of the trip. 

We finished things off by flying United HNL-EWR in Economy Plus and we spent a few days in New Jersey before driving back to Boston. All in all we were away from home for 18 days. Hopefully that gives you enough context for my thoughts and tips for traveling with a toddler (and two other kids!). Okay, here are my totally random thoughts!

Choose a destination that minimizes stress 

Different parents and their children deal with stress differently. What may stress out one family may be totally cool for another and vice versa. You know your family best so make sure you choose a destination that will stress your family out the least. 

For us, at this stage in our lives, that meant traveling somewhere where we felt comfortable communicating. Hawaii is far, but it’s still the United States and we didn’t have to layer in an extra level of stress. The more kids we’ve had, the less “brave” we’ve been on our trips. The first two kids both visited Asia before they turned two, but the baby will have to wait a little bit.

People like to recommend the “best” destinations for kids and in general they’re probably right, but you know your family best so pick a destination that minimizes your stress!

Don’t plan too many activities (especially when traveling with a toddler)

In that vein, we’ve really evolved into focusing on one or two planned activities per day. When we used to travel even with only one child, we still were able to plan like we used to – jam packed activities all day with a nap in the middle. But with three kids in tow, we’ve found the best policy is to plan one morning activity and then let the rest of the day play itself out. I’ve found that if we plan activities but don’t get to them it feels disappointing. On the other hand, if we end up doing extra activities because we’re having a good day, it feels like finding money on the street.

That’s not to say we don’t plan any busy days on our trips anymore. But what’s happened is that on a typical day, we’ll plan for one or two activities max. Every once in awhile, of course, we won’t have a “typical” vacation day and will plan to go all out activity wise. But the overall activity per day average is just way lower when traveling with toddlers than it used to be or than it even is when traveling alone with the six year old.

Naps are important for the long run

Years ago, my esteemed Disney podcast co-host wrote about not stressing the nap when flying with toddlers, and I’ve lived by that policy since my kids were born. But don’t mistake not stressing the nap on the flight for not stressing the nap throughout the vacation. Kids can survive a flight without napping if necessary, but if they miss nap day after day on vacation, it all ultimately ends in tears. With my kids, at least!

That means on the ground we prioritize getting naps on most days. That dovetails nicely with planning only one or two activities per day. It also means if we have the time, we’ll try to take a nap or at least quiet time even if a day is going well. It’s worth it for the long term benefits in my opinion.

In Hawaii, of course, this was relatively easy. Sometimes my oldest daughter would stay out by the pool with one of us, but for the most part, since we mostly spent time at the pool or beach, we made it a point to get back to the hotel room every afternoon.

The stroller is your friend (especially with jet lagged toddlers)

Both in Hong Kong when our son was 20 months and in Hawaii when our youngest was 20 months we found stroller naps to really help with the jet lag. Older kids, even three year olds, can sort of listen when you say they have to sleep or have to lie down even when they’re jet lagged. In a worst case scenario you can have a three year old watch a tablet at 3 AM when they should be sleeping.

Not so when traveling with toddlers! Most don’t have the attention span to watch a tablet quietly which means they’ll wake up their siblings. When our kids were still jet lagged we only had the one hotel room, so when my daughter woke up at 2 AM I had to do something with her that didn’t wake up the other kids or my wife. 

And that’s the story of how I found myself wandering Waikiki and the beach at 230 AM. (Also, the same thing happened in Causeway Bay in Hong Kong in 2017 with my son). Having a good stroller really helps, even a jet lagged baby can usually sit quietly in a stroller for a good amount of time. So even though we didn’t sleep, she at least was able to be calm and to rest. I would have preferred to sleep but walking along the boardwalk with the sound of waves at night wasn’t too bad all things considered.

All three of our kids growing up got very accustomed to stroller napping so we also used the stroller to help the baby nap during the day. So, make sure you get yourself a good stroller! We’ve been using the same Uppababy G-lite (Amazon affiliate link) for six years now – but just get the stroller that works the best for you.

Be prepared to eat at the hotel more than you might like

Before we had kids, I don’t think we ever ate at the hotel outside of a complimentary breakfast. But we’ve found there’s an inverse relationship between the number of children we have and the amount of times we end up eating at the hotel. This effect is even more exaggerated when traveling with toddlers. For us, eating at the hotel means both eating in the hotel restaurants and getting takeout and bringing it back to the hotel lobby or our hotel room.

This of course boils down to simple logistics. Sure, we had a very portable carseat and two boosters, but without a car we still didn’t Uber or Lyft out of the hotel much. At times we split the team, I’d walk with one kid and the stroller to a place off property we were eating while my wife would catch a ride, but still: getting off property is annoying with three kids. Especially when one’s a toddler!

Even when we had a car at Aulani, the activation energy required to get everyone in the car was often high enough that we didn’t bother. So we ate at the hotel quite a bit or I would run out, get food, and bring it back. It just made life easier.

I have a corollary to this. We love to eat and certainly eating amazing food we can’t get home is part of the draw of vacation. But I’d rather get a B+ meal and minimize the disruption to the kids than get an A+ meal and risk a meltdown. And when you’re in a place like Hawaii, it was easy to find unique foods that we couldn’t get in Boston without pushing our kids too hard. Thus – taking food back to the hotel when we wanted something more Hawaiian and just eating at the hotel when we just needed food in our bodies.

Expect only one parent to be on vacation at a time

There’s been a lot of ink spilled about whether traveling with toddlers or just kids in general qualifies as “vacation”. To me, I just love seeing new places and getting out of our normal routine and I don’t worry too much about labels.

But, and this is a big one, if you think of “vacation” as relaxing, chilling out, and enjoying yourself, I’d say that with a toddler (and no babysitting) you can expect that only one of the parents will be on vacation at any given time. Just like at home, if one parent watches the kids the other can go relax and enjoy themselves. That’s how we’ve been doing things on vacation since the first was born. Sure, you’ll catch moments where the kids are all happily occupied and the two parents can be on vacation together, but for the most part, you’ll probably only have one person in full on chill mode at a time.

That’s why if it’s possible, bring grandparents or hiring babysitting so at least you get some time to vacation together!

Norms and rules from home? Let them go…

My last bit of advice relates to norms and rules you have at home. I think most families do this, but when we’re traveling, most of our norms and rules go out the window. The biggest example of this on this particular trip was the pacifier. Our other two kids were weaned off of the pacifier before they hit 18 months. We didn’t wean the youngest off the pacifier until after Hawaii, when she was about 21 months. It just was worth having that actual crutch for the long trip.

Here are other norms and rules we let go in Hawaii:

• Ice cream every day
• Variable bed times
• Unlimited screen time on flights
• In room movies almost every night (free DVDs to borrow at both resorts)
• More snacks and chips than usual
• Buying random stuff to keep the kids happy 
• What is a vegetable?

Essentially, a lot of small things that we draw lines about at home, we let go while in Hawaii. In the end, we figure we’re on vacation and we can “fix” bad habits when we get back. And I’m happy to report that for the most part we have!

Final Thoughts

In the end, these are the things that have helped us most as a family when traveling with toddlers. It’s tough to believe we’re almost out of this stage – maybe we’ll squeeze a couple more international trips before our youngest starts having some modicum of reason. But the reality is, toddlers don’t understand reason, that’s why over time we’ve found the above strategies worked best for our family.

What strategies did you use when you traveled your kids as toddlers? Let me know in the comments!

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