The Daddy-Daughter Road Trip:(And the Glorious Detour into Chaos)

There are moments in parenting that feel like they should come with a soundtrack. You know, one of those triumphant orchestral scores that swells as you hoist your kid into the car seat and proclaim, “We’re going on an adventure!”

That was the energy I brought into our very first daddy-daughter road trip. I had a plan. A good plan. A great plan, even. A plan so foolproof that not even a toddler could derail it. Which, in hindsight, is the kind of confidence that deserves its own category in the museum of bad parenting decisions.

The Grand Plan: Drive to Michigan to visit the in-laws (her grandparents). Break up the trip halfway with a hotel stop. Swim in said hotel pool (her first real hotel pool experience). Jump on the bed like it owes us money. Order pizza. Eat it. Laugh. Bond. Fall asleep watching a wholesome movie. Wake up refreshed and full of memories.

What could go wrong?

The Packing: You don’t realize how much crap a tiny human requires until you try to pack for one overnight. I brought:

• Four outfits for her (because spills, tantrums, and the laws of physics).

• One outfit for me (because I’m a dad and clearly not planning on sweating or spilling anything).

• Two pairs of shoes for her.

• Swim gear, floaties, snacks, wipes, iPad, stuffies, blanket, backup blanket in case the primary blanket somehow offends her.

And so we set off. Me and my toddler, armed with snacks, high hopes, and a playlist that alternated between Encanto and whatever I could sneak in when she got distracted.

The Drive: Let’s talk about road trip conversations with a toddler. They go something like this:

“Are we there yet?” “No, honey, we just left.” “Oh. Are we there now?”

Repeat for 132 miles.

Also: the snack schedule. She ate all her snacks before we hit the city limits. So the rest of the drive was a delicate dance of bribery, storytelling, and desperate singalongs to the Moana soundtrack.

The Hotel Arrival: If you’ve never shared a hotel room with a toddler, let me paint the picture. It’s like being trapped in a very small amusement park with no off switch. Every drawer is a mystery. Every button must be pressed. And the elevator? The elevator is a gateway to joy, madness, and stopping on every single floor for absolutely no reason.

But I promised her swimming. She’d been talking about it for weeks. So after unloading the entire backseat (which looked like I was fleeing a house fire), we got into our swim gear.

The Pool: Empty. Beautiful. The dream scenario.

She approached the pool with all the enthusiasm of someone being led into a dentist's office. And then she cried. And cried. And cried some more.

To be fair, she’s in a phase where even the suggestion of a new experience can bring on tears like she’s auditioning for a toddler soap opera. But we sat on the edge. I splashed. She glared. I got in. She watched. I coaxed. She dipped a toe. And eventually, she clung to me like a baby koala and agreed to “swim” (read: be held in the water while yelling, “Don’t let go!” every 4.5 seconds).

She laughed. She splashed. She screamed once when a water bubble surprised her. But she did it. And that was enough for me.

The Bed Jumping and Pizza Debacle: Back to the room. High energy. She bounced off every surface like a pinball with legs. I, in my infinite dad wisdom, ordered a large pizza assuming she was as hungry as she was loud.

She ate half a slice.

I stared at a mountain of pizza like a man who’d just realized he forgot what portion control meant.

The Sleep Attempt: Nothing tests your sanity quite like trying to get a toddler to sleep in a hotel room. You’re lying six inches away, breathing too loud. The TV’s on for comfort. That just turns into another reason she won’t sleep.

Turn it off? Now we have questions. Endless, soul-piercing questions.

Eventually, somewhere between a lullaby and her asking if ghosts are real, she passed out. Sideways. Like a tiny drunk octopus.

I lay there, half-hanging off the edge of the bed, staring at the ceiling and thinking, We did it. We’re alive.

The Morning: She woke up in a great mood, declared the hotel the best place ever (now that she didn’t have to swim again), and we went downstairs to share a hotel breakfast that was 90% toast for her and 3 cups of coffee for me.

The second leg of the trip? Quiet. Peaceful. Dare I say… pleasant? We talked. We sang. We waved at cows. We made it to the grandparents’ house with no meltdowns and only minor emotional scarring.

The Takeaway:

Was it perfect? Not even close. Was it messy and chaotic and exhausting? You bet. Would I do it again tomorrow? In a heartbeat.

Because that’s the thing about these little parenting adventures: they’re rarely about the plan. They’re about the moments. The missed exits. The hotel hallway races. The way she clung to me in the water but also how she smiled when she finally kicked her feet.

We’ll do another one. And another. And I’ll keep pretending I can make the perfect plan.

But deep down I know: it’s the detours that make the best memories.

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Today’s Cocktail: The Hotel Hallway Hurricane

• 1 oz dark rum

• 1 oz coconut rum

• 1 oz orange juice

• 1 oz pineapple juice

• ½ oz lime juice

• Splash of grenadine

Shake it like a toddler resisting bedtime. Pour over ice in a plastic hotel cup you’ll probably forget to return. Sip while listening to the sound of tiny feet running down the hallway.

Cheers to road trips, resilience, and really, really cold hotel pools.