In the annals of family vacations, there are trips that go smoothly and leave behind picture-perfect memories—and then there are the trips that turn into chaotic, laugh-out-loud stories that get retold at every holiday dinner for the next twenty years. The Gutfeld family’s first trip to Disneyland firmly belongs in the latter category.

What was supposed to be a whimsical, joy-filled experience at the happiest place on earth quickly spiraled into a comedic odyssey filled with missed flights, broken phones, meltdowns (both child and adult), and moments of unexpected joy that reminded everyone what truly matters.

The Best-Laid Plans…

Greg Gutfeld—known for his sharp wit and no-nonsense commentary—probably didn’t expect that the biggest challenge he’d face this year wouldn’t come from political discourse, but from a three-year-old, a TSA checkpoint, and a malfunctioning iPhone.

It all began, as many travel horror stories do, with a missed flight. The Gutfelds, running on limited sleep and overstuffed luggage, arrived at the airport later than planned. Between Greg frantically checking in online, luggage tags disappearing, and a toddler demanding snacks at peak meltdown hour, the family missed their boarding call by mere minutes.

Cue the airline shuffle: rerouting, standby lines, and trying to explain to a small child why they couldn’t just “take a different airplane.”

“It’s okay, Daddy,” little Mira reportedly said, “we’ll fly with the birds.” Greg wasn’t sure whether to laugh or cry.

A Digital Disaster

If there’s one thing a modern traveler relies on, it’s their phone. Maps, tickets, itineraries, mobile check-ins, entertainment—it all lives in your palm.

So naturally, in the cruelest twist of fate, Greg’s phone chose this exact moment to give up on life. Not a soft malfunction, either—this was full-screen blackout, never-turning-back-on failure.

With no access to hotel bookings, theme park tickets, or even directions to the rental car, the Gutfelds found themselves thrust into analog mode. Paper maps were hunted down like rare artifacts. Strangers were approached for directions. It was the 1990s all over again.

Still, with humor and resilience (and a few panicked calls from borrowed devices), they finally made it to Anaheim.

The Magic Begins… Kind Of

Day one at Disneyland didn’t start smoothly either. Mira, dressed head-to-toe in Minnie Mouse gear, was beside herself with joy—until she saw the crowd. The sheer volume of people, costumed characters, and loud noises led to a meltdown that echoed through Main Street USA like a siren warning incoming doom.

But here’s the thing about kids: their moods turn on a dime.

Just as quickly as the tears came, they disappeared. Mira spotted a balloon vendor. Her eyes lit up. Within minutes, she was laughing, spinning in circles, her balloon floating above her head like a beacon of childhood joy.

Greg, exhausted and probably regretting not booking a beach vacation instead, looked on in disbelief—but also, perhaps, with a small smile.

The Ride Roulette

Theme parks are a strange cocktail of joy, fear, and relentless walking.

The Gutfelds tackled ride after ride, each one bringing its own set of adventures. Mira declared “It’s a Small World” the greatest artistic creation in human history, while Greg endured the earworm soundtrack with the dead-eyed stare of a man being slowly driven mad.

The family barely survived the Mad Tea Party’s spinning teacups without a gastrointestinal incident, and Pirates of the Caribbean sparked Mira’s new obsession with pirates (“But good pirates, Daddy, like the ones who say ‘please’ before taking your treasure”).

Greg’s wife, Elena, seemed to be the only one keeping everyone on track—booking Lightning Lane passes, organizing meal breaks, and wrangling stroller traffic like a military strategist.

The Small Moments That Matter

And yet, amid the chaos, the missed naps, the overpriced churros, and the repeated losing of hats, something quietly magical began to happen.

On the second day, Mira watched a parade float go by and spontaneously shouted, “This is the BEST DAY EVER!” at the top of her lungs. Strangers clapped. Greg cried (he won’t admit it, but witnesses confirm).

The family ended up stuck in line for over an hour for a princess meet-and-greet, only for Mira to become starstruck and refuse to speak when finally face-to-face with Cinderella. It was awkward. It was adorable. It was real.

And in those little in-between moments—sitting on a bench sharing ice cream, watching fireworks light up the sky while Mira gasped in wonder—everything slowed down.

The phones, the flights, the frustration—they faded. What remained were smiles, silly photos, sticky fingers, and memories that couldn’t be engineered or scheduled. They just… happened.

Reflections From the Exit Gate

By the final day, the Gutfelds were walking a little slower, laughing a little louder, and learning that even a vacation that feels like it’s falling apart can stitch a family closer together.

Back at the airport, as they waited (very early this time) for their return flight, Greg summed it up perfectly:
“We missed the plane, I broke my phone, I probably spent more on snacks than on park tickets… and I’d do it all again tomorrow.”

Mira, holding a plush Mickey in one hand and a half-eaten lollipop in the other, nodded solemnly.

“Next time,” she said, “we bring Grandma.”

Greg looked terrified.

The Takeaway

The Gutfeld family’s chaotic Disneyland trip wasn’t perfect—but maybe that’s exactly what made it perfect. It wasn’t about the rides or the Instagram-worthy moments. It was about being together, getting through the madness, and finding joy in the mess.

Because sometimes, it’s the trips that go completely wrong that end up being the most right.