Travel With Kids Feels Overwhelming? How Squish Travels Helps You Find Meaning Over Perfection

The Moment We Realized Something Wasn’t Working

We used to think traveling as a family was supposed to feel magical. Everyone tells you that traveling with your child is how you “make memories,” how you “give them the world,” how you “soak up every moment while they’re little.”

But the truth?

Most of the time, it didn’t feel magical at all. It felt overwhelming.
We’d pack for days, stress about the car ride, worry about naps, snacks, moods, timing, weather, and all the little things that never seem to go as planned.

And somewhere along the way, we noticed we weren’t actually living the moments we were trying so hard to create.

We were surviving them.
Going through the motions.
Trying to keep everything “under control” enough to count as a good memory.

And then one day, honestly, in the middle of yet another frantic travel morning, we had a lightbulb moment.
We looked at each other and realized:

This isn’t the way we want to travel as a family.

This isn’t the way we want our son to remember these years.

And it doesn’t have to feel this way.

That realization changed everything for us.

Because travel wasn’t the problem.
The pressure was.

The Day We Decided Something Needed to Change

Once we realized we were drowning in the pressure to “do family travel right,” we had to make a choice:

Either keep white-knuckling our way through trips,
or
rebuild the entire meaning of what travel was supposed to look like in our family.

And the moment we gave ourselves permission to redefine the goal, everything softened.

We stopped chasing perfect itineraries.
We stopped obsessing over how long the drive would take or whether every moment would be “worth it.”
We stopped expecting our child, our sweet boy, to magically be someone he wasn’t just because we were “on vacation.”

Instead, we asked ourselves one simple question:

What if traveling wasn’t about perfection at all…
but about being together in a way we rarely get to at home?

That shift changed the energy in our home, our car, and honestly, our hearts.
And that shift became the foundation of Squish Travels.

Squish Travels: Finding Meaning in the Journey, Not Perfection

Traveling with kids can feel overwhelming…
but it doesn’t have to.

And Squish Travels exists to help families like ours, families with one child, busy schedules, stretched-thin parents, and big dreams, find a way to explore the world without losing ourselves in the process.

Here are the core ideas that changed family travel for us
(and that we will explore deeper in future posts):

1. We Created a “Travel Rhythm”, Not a Plan

Most trips fall apart because the plan is too tight…
and real life with kids is anything but tight.

Instead of planning every hour, we created a travel rhythm, gentle anchors for the day that support our son and take pressure off of us, like:

• Morning movement (a short walk, playground, exploring the hotel hallway if needed)

• A built-in quiet time each day

• A “one adventure” rule instead of packing the schedule

• Each person picking one thing they’re excited about (yes, even kids!)

• A calm nighttime routine that mimics home

This rhythm gave us structure without suffocating us with expectations.
It gave us space to breathe.

And honestly? It made travel feel possible again.

2. We Turned Car Time Into Connection Time

For years, we treated the car like something to “get through.”
But kids, especially boys, often open up best when they’re side-by-side, not face-to-face.

So we shifted our mindset and turned the car into a bonding space instead of a stress zone.

Some of our favorites that changed everything:

• Conversation cards designed just for car rides

• Story-building games

• Snacks that feel like a treat

• Letting our son help “co-navigate”

• A travel playlist we built as a family

It sounds small,
but the conversations we’ve had in the car are some of the best we’ve had all year.

3. We Redefined “Worthwhile Travel”

We used to think a “real trip” meant plane tickets, hotels, and tons of planning.

But our son doesn’t see it that way.

For him:

A one-hour drive is an adventure.
A new park is an adventure.
A breakfast picnic is an adventure.
A quick weekend trip is an adventure.

Once we stopped chasing the “big” trips and started embracing the nearby ones, travel became something we could do more often, and with way less pressure.

4. We Made Travel About Growth, Not Perfection

This was the big one.

We realized our son doesn’t learn from perfect trips.
He learns from the messy parts:

• Delays

• Weather changes

• Detours

• Boredom

• Waiting

• Flexibility

Travel became less about “everything going right”
and more about helping him build resilience, curiosity, and adaptability.

And in that shift?

We grew too.

5. We Started Tracking Our 50 States Goal

This created excitement, momentum, and a sense of togetherness.

We printed a map, hung it up, and started checking off states together.
It gave our son something to look forward to,
and it reminded us that progress matters more than perfection.

Some trips are messy.
Some trips are magical.
All of them count.

Our Message to You

If traveling with kids feels overwhelming,
please hear us when we say this:

You are not a bad parent.
You are not doing it wrong.
You're just carrying too much pressure.

We’ve been there, truly.
And we are still learning, still growing, still imperfect in all the same ways.

But when we slowed down, shifted our expectations, and made travel about meaning instead of perfection… everything started to change.

We laughed more.
We argued less.
We connected deeper.
We enjoyed our son more.
And he enjoyed us more too.

And we want that for you.
Not the perfect trip.
Not the Pinterest itinerary.
Just the gift of being together in a world that keeps pulling families apart.

You deserve trips you don’t have to recover from.
You deserve memories that feel light instead of forced.
You deserve a version of travel that fits your real life, not the life Instagram says you should have.

And if any piece of today’s post made your shoulders soften just a little…
then you’re already on the right path.

Your next step?
Choose one tiny shift, just one, from this list.
Try it on your next drive, next outing, next weekend adventure.

Small changes create big connection.
And we’ll walk with you through every step of it.

You’re not alone in this.
You’re doing better than you think.
And we’re cheering you on, every mile of the journey.