6 lessons from 11,180 miles with two toddlers

We’ve been on over 50 flights since our first child was born in 2014. These adventures have included projectile vomiting on Singapore Air (the one time, we upgraded to business), questionable car seat decisions, and 832 walks up and down the aisles while counting down the number of 7 minute increments until you land. Yet one pattern emerges during every vacation: a blow out fight on the second day. Every. Single. Trip.

A small part of me celebrated when I saw this vacation tweet from RadReader Jeremy Walter about his family jaunts:

I mean, isn’t RadReads about not feeling alone in one’s suffering? Jeremy inspired me to share our own travel learnings – and if the inevitable “Day Two” lovers’ quarrel is worth it.

The most appropriate aphorism

Remember that time before you had kids when parents thought they were being helpful by peppering you with random parental aphorisms? These tips were typically met with an internal eye roll – not out of disrespect – but out of the complete inability to relate with the seismic forthcoming life change.

One of these aphorisms has stood the test of time: It’s not a vacation, it’s a trip. And since our kids have been born, we’ve gone on two vacations (i.e. no kids) and a dozen of trips (including a month-long, multi-city summer adventure). Here are six lessons from these adventures:

1. Expectations, meet reality

Super blogger Tim Urban formulaically defines happiness as reality minus expectations. And when you embark on that vacation trip, the expectations are high. Kindles loaded with beach reads. A new Lulu workout outfit. Paper magazines from the airport. And limitless permutations of sugary cocktails.

Yet day two of the vacation trip sends the expectations through a buzzsaw. As Mike Tyson reminds us, “Everyone has a plan, until they get punched in the mouth.”

And boy does day two deliver a knockout. Expectations, meet Reality. It turns out you can only pick one (and nope, there will not be any reading on this vacation trip):


  • A quiet coffee with your morning paper
  • A relaxing evening cocktail
  • A half-assed (and abbreviated) workout


Pairing this realization with the inevitable sleep deprivation sets the vacation trip up for the Day 2 blow out.

2. It’s like guarding Steph Curry

What about the flights, you ask? They’re actually deceptively straight forward (that is, unless you encounter a napping failure). Take your trip time (i.e. CPH to LAX is 11 hours), convert it to minutes and divide it by 7.

Why seven? If you’ve got a child who isn’t iPad distractible (i.e. under the age of 3), the burden of entertainment will fall squarely on you. And our empirical observation is that you can entertain said child for seven minutes, before they demand the court jester find something new.

Since 11 * 60 / 7 equals 94, you are now tasked with finding 94 activities with your little one.

Trip to the bathroom. One.

Playing with two cups. Two.

Opening and closing an Airpod case. Three.

(All while playing defense so they don’t poke the skeptical passenger next to you).

Lather, rinse, repeat. To call a long haul flight a marathon is a gross understatement. It’s more like guarding Steph Curry during the NBA finals.

3. You will listen to A LOT of podcasts

I recently tracked a friend’s vacation on Instagram. It was a series of idyllic tropical posts of a toddler, but read no further than the caption to see what was hiding in plain sight. Day one was welcomed by a 1 am wake up time. Day two improved to 2 am. Lather, rinse, and repeat.

Two words scare the bejesus out of vacation trip-bound parents: Jet Lag. And here’s the dirty little secret nobody talks about. When you were single, recovering from jet lag was straightforward. Sleep when you’re tired, wake up when you’re not.

With kids, you’re a prisoner to the lowest-common denominator. You don’t get to recover from jet lag until they recover. So fire up those podcasts!

4. IDGAF about fancy

When we were in New York, I dragged my five year old on elaborate scavenger hunts. Each night, we’d go on ice cream tasting tours alternating between Ample Hills, Van Leeuwen, Daveys, and Odd Fellows.

Her tiny toddler palate sampled the craftiest of craft ice creams on the reg. Yet her favorite? The 99 cent shaved ice, doused in pink high-fructose corn syrup.

The only thing that matters at a hotel is a diving board. At a restaurant, chicken fingers. And in a rustic European capital, the local playground.

5. Intimacy evaporates

During any vacation trip, parents are re-born as air traffic controllers. By opting out of your home, you forgo the rights to infrastructure (i.e. high chairs), structure (set nap times) and most importantly: child care.

Any parent will know that having a conversation that doesn’t cover poop frequency and pick-up logistics is at a premium when you’re at home. Now transport your motley crew into an unfamiliar setting, thousands of miles away.

For us, baby sitters on vacation have never really worked. Like snowboarding, there’s definitely a flow state to be had — but the learning curve is steep AF. Said differently, your butt will hurt for the first few attempts. So hiring a babysitter through a friend or hotel concierge didn’t clear the break-even calculation. (And this doesn’t cover the inevitable meltdown when the stranger first enters the room.)

6. The vacation starts when you get home

The tears will start streaming down the parents’ faces when they arrive home, greeted by their own car seats, toileteries, reliable WiFi, and baby sitters on speed dial.

So here’s an honest question: Why do it? Why on earth would a family opt into this masochistic meat grinder?

It’s easy. It’s actually not a trip, nor is it a vacation. It’s an adventure. And adventures, by definition, require movement and leaving what you know behind. Even it’s for a. week.

The collective “struggle” teaches us to collaborate. Breaking out of routine irgnites countless banter about the vastness of the world and the expansive beauty of the people who inhabit it. And as parents, we get a front row to the firing of their tiny synapses, the wonder in their eyes, and the joy of unconstrained curiosity and discovery.

It really is a vacation trip, man.

Shout-out to Dan Putt, who helped inspire this post.



For instant Access, Enter your Details Below:

🔒 Privacy Protected by our “Zero Spam” Policy

For instant Access, Enter your Details Below:

🔒 Privacy Protected by our “Zero Spam” Policy