When Family Travel Doesn't Go As Planned...

Letting go of expectations & the messy realities of traveling with kids.

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It’s been five years since our family took what I’d call a real trip. In between a global pandemic, a cross-country move & two home renovations, life just felt too chaotic to take on anything more. But before all that, travel was just something we did. We even prided ourselves on it, seamlessly navigating airports with strollers, travel cribs & a stash of diapers in tow.

So when we finally boarded a plane for Boston & Martha’s Vineyard earlier this month, I felt this huge sense of relief. We were finally getting back to something we absolutely love doing as a family.

But what I didn’t realize is that I’d been holding on to this old script of sorts by picturing a return to ourselves & the thing we love most to do together. In fact, with the kids being so much older now, I mistakenly assumed it would be even easier than ever before.

And honestly? It just wasn’t. It might have been our toughest trip to date. But through the moments that were hard, I walked away with some clarity that I think will make our future trips a little easier—and maybe my takeaways will help you, too.

When family travel doesn’t go as planned.

Now here I am, a week post-travel, ready to share my takeaways from a family trip that was fun, but honestly, less than spectacular. So this is my exercise in letting go of the idea that vacations have to be spectacular.

I know family travel can be hard, and I walked away from this experience with some thoughts that might help you take your own trips in stride—to see the challenges not as a personal failing, but as the simple reality of traveling with kids.

Travel is a muscle.

Use it or lose it. If we aren’t traveling with our kids regularly, they won’t have the stamina for the busy, on-the-go days that come with it.

My family is the perfect example. My son has been lucky enough to keep traveling over the past few years, continuously strengthening his travel muscle. My daughter, however, was only three when we curbed our family travel; she hadn’t done a trip like this since. And now that she’s nine, she’s in the position of not being used to the fast pace, the shorter nights of sleep, the lack of her creature comforts, or the lost sense of autonomy over her time. It’s a lot to be thrown into and be expected to just hold it together.

This trip was trial by fire for her, and it served as a powerful argument for more regular family travel—not just to build that muscle, but to keep it from atrophying.

Travel is overstimulating.

To kick off our trip, we went straight from our quiet home in rural Colorado to the heart of a big city. It was eye-opening how all four of us remarked on the noise and overwhelming energy. Jason worked and lived in downtown Chicago for decades, and we raised our kids on regular city weekends.

But after just four years away, we all felt how sensitized we’d become. It helped me realize that if I was feeling this as an adult—able to make sense of it and decide when I’d had enough—it must be infinitely harder for our kids.

This applies to any new setting. A change in environment, a disruption to routine, and a flood of new experiences will naturally tax a child’s nervous system. So if you’re on a trip and your child is melting down more, complaining a lot, or even eating less, remember these can be signs that travel is just a lot. Meeting them with compassion and building in extra downtime can make all the difference.

Travel is a case study in emotional regulation.

Overwhelmed nervous systems naturally lead to hijacked emotional regulation. Cue the tears, the complaining, the digging-in of heels, and the flat-out defiance. You know your child’s default settings, so fill in the blanks there.

This trip was a reminder that it’s not just our kids’ emotional intelligence being tested, but ours, too. We’re not only managing our own feelings around delayed flights, car rental mix-ups, or subpar restaurant meals; we are also the person our kids look to when they’re dysregulated.

One of our most important jobs is co-regulation. When our kids are spiraling, they look to us to model calm in our own bodies and behavior. And there is almost nothing harder than trying to be the calm when you’re already emotionally fried. It’s a fragile dynamic.

I was confronted with this reality constantly. There were moments I felt proud of myself for recognizing my role as co-regulator, which helped me stay calmer than I otherwise would have been. But as the trip wore on and my own self-regulation wore down, it became harder to be the calm presence my kids needed.

And hey, it’s human to lose your patience. I definitely did on this trip, and I still don’t feel good about it. But I have to remind myself that research shows the real power is in the repair. When I have my own moments of dysregulation, taking the opportunity to apologize and show my kids what it looks like to own our behavior is deeply impactful.

Making travel a little easier

No trip is ever going to be perfect. When things get tough, remember: travel is a muscle, it’s overstimulating, and it will challenge even the calmest family. If you’re struggling, it isn’t you. It’s just the nature of traveling with kids.

Here are 10 things I did in the moment to try and make it easier:

1. Remind myself that behavior isn’t a power play (even when it feels like one). It’s usually a symptom of an unmet need.

2. Baby them. Not literally, but when our kids are dysregulated, we have to take our support several steps back. That might mean extra cuddles, a piggyback ride, or a special treat to get them through.

3. Rely on ChatGPT. It’s great for spur-of-the-moment entertainment ideas when your own brain is fried (e.g., "Give me a 5-minute scavenger hunt for a hotel room").

4. Ease up on screen time rules. Travel often requires more sitting still than usual. It’s okay to provide extra entertainment to get through a long dinner or train ride.

5. Give them a sense of autonomy. Invite them to choose the next activity, the route you take, or the museum exhibit you see.

6. Be silly. Pull out all the stops to get a laugh and disrupt a negative pattern for everyone.

7. Validate their feelings. Let them feel seen and understood. It doesn’t mean you have to change the family’s plan, but it does mean you honor that their feelings about it are valid.

8. Break off from the group. Go on a mini-adventure, just the two of you, on a "mission" to find something you need their help with.

9. Take on a new persona. Every afternoon when we were back at our rental to rest, I’d pretend I was the kids’ British nanny. By adding a touch of play to an everyday interaction (showering, getting a snack), I was one degree removed from ‘Mom,’ and they were calmer, more playful, and far more compliant.

10. Wrap things up early. It’s always better to end on a high note and get the rest and downtime everyone needs.

And now that I’ve had the week to decompress, I think I’m walking away with a renewed purpose to travel more regularly... Letting go of the pressure for it to be easy or perfect is the first step. Because it’s not going to be seamless but I can’t let that be what stops me & my family from traveling more.

I’ll be honest, some moments on this trip were miserable. There was one night in particular that we’d really been looking forward to. We’d planned to spend the evening at Fenway Park—it was over 90 degrees, so humid, at the end of an already long day & Stella was decidedly not having it.

And yet, in the midst of her exhaustion, she somehow befriended a security guard who got her onto the field to meet the mascot. She navigated her food allergies & charmed her way onto a private deck to get the Icee her heart was set on. Then the whole night ended abruptly in a third-inning rainout that sent us scrambling into a soggy, cramped taxi. But we were leaving earlier than planned, which for her (and for me, if I'm being honest) was a secret win.

It’s not the perfect ballpark memory I might have planned, but it was something else entirely: messy, surprising & a reminder that the best moments are rarely the ones we’d planned for in our itinerary.

And that, I'm realizing, is what makes it all worthwhile.

If you have some of your own strategies that have helped make family travel a little easier, please share them in the comments! I’m crowd-sourcing for myself, and I know everyone else here would appreciate the ideas.

And if you’re heading out of town for an end-of-summer getaway, let me know where you’re headed! I love hearing what your family is up to. 🥰

Keep simplifying,

Erin