We Let AI Plan Our Family Trip… It Went Off the Rails
What happens when you let artificial intelligence plan a family vacation with zero backup plan? We wanted to find out.
With one weekend to spare and a family full of different preferences (and let’s be honest, strong personalities), we handed over full control to ChatGPT. The plan: a 24-hour trip to Charlotte, North Carolina, fully designed by AI. That included meals, lodging, activities, and even dietary accommodations.
This wasn’t just an experiment in convenience; it was a test to see whether AI could juggle real-life family chaos. Here’s how it went.
Meet the Cast of This Chaos
Our family isn’t exactly easy to plan for:
Miss Bossy Pants
SIBO Queen (special diet = special challenges)
Displeased Anna (hard to impress)
Control-y Steve (don’t ask)
Party Pooper (stayed home to play video games…)
Our needs ranged from “I want steak” to “I need church” to “I have a 48-hour video deadline.” So naturally, we let ChatGPT sort it out.
Needless to say, planning this trip manually would’ve been a headache. So we asked each family member to submit their preferences directly to ChatGPT and let the AI build an itinerary that could, hopefully, keep everyone happy.
How We Used AI to Plan the Whole Thing
Instead of spending hours researching restaurants, searching TikTok for activities, and texting back and forth about what to do, we asked ChatGPT to do it for us. The goal was to simulate what a deeply personalized travel assistant might offer: researching restaurants that met our dietary needs, finding activities that matched our interests, and mapping it all around our specific timeframe and location.
The trick was giving ChatGPT detailed prompts from each family member. It then generated a full itinerary, including hotel recommendations, restaurant menus, driving times, fun stops, and church service options. It even suggested music for the drive.
Camera Gear We Took Along
As content creators, we brought along some key gear to document the trip. The MVP of the weekend was the DJI Osmo Pocket 3: a compact, gimbal-stabilized camera that made it easy to shoot high-quality video while traveling light. It’s small enough to be non-intrusive in public, and its time-lapse and hyperlapse features were perfect for capturing the drive.
We paired it with DJI’s wireless lav mics for clearer audio and packed a DSLR camera as backup, though we didn’t end up using it. When you’re chasing kids around a city, the smallest setup usually wins.
Arrival in Charlotte: Grand Bohemian Hotel
Our first stop was the Grand Bohemian Hotel in downtown Charlotte, another ChatGPT recommendation. Honestly, it was a hit. Stylish interiors, clean rooms, and a central location made it easy to drop our bags and get moving.
For a family that’s admittedly picky about hotels, this one earned universal approval.
Dinner at Porter’s House
Dinner was also a success. Porter’s House checked all the boxes: a steakhouse atmosphere for the fancy eaters, a menu that included SIBO-friendly options, and enough variety to satisfy everyone.
One of us used ChatGPT to scan the restaurant menu ahead of time and even asked for custom recommendations based on dietary restrictions. That level of detail helped us avoid food-related issues the entire weekend.
Church and Hotel Downtime
On Sunday morning, a few of us went to Elevation Church, a high-production service that streams across multiple platforms. It was impressive to see the level of equipment and video production in person. Meanwhile, the rest of the family relaxed at the hotel, complete with hotel robes, slippers, and a quick workout.
The Brunch Debacle
This is where things got messy.
ChatGPT’s top brunch suggestion was The Famous Toastery, which turned into a wild goose chase. After struggling to locate the place, we ended up walking through back alleys, crowded parties, and some pretty questionable areas, not exactly ideal with kids in tow.
We finally found the restaurant, but the vibe didn’t match the expectations. We decided to skip it entirely.
Brunch Recovery: Burton’s Grill
Thankfully, there was a second option: Burton’s Grill. This place delivered. The staff were incredibly accommodating with custom meal requests and even built SIBO-compliant plates from scratch. Everyone left full and happy, except for the coffee, which didn’t pass the test.
Still, this stop was a redemption moment for the AI-generated itinerary.
Museum of Illusions
Next up was the Museum of Illusions, selected for being fun, family-friendly, and full of Instagram-worthy photo ops. For the most part, it lived up to the hype. The interactive exhibits were a hit with the kids, especially the mirror maze and optical illusions that reminded us of old-school film techniques.
That said, the experience was dampened by the overwhelming smell in the building, one of those unpredictable realities AI couldn’t factor in.
IKEA (and the Unexpected Plot Twist)
We almost skipped IKEA at the end of the trip, but figured we’d make a quick stop to grab a desk. When we pulled up, the store was being evacuated. Fire trucks. Crowds. Chaos. It felt like a movie.
We captured a few clips with the Osmo Pocket, but didn’t end up buying anything. Instead, we learned that IKEA can deliver, saving us the trouble altogether.
Final Takeaways
Despite a few hiccups, ChatGPT pulled off a surprisingly successful trip plan. It managed:
Hotel and restaurant bookings based on dietary and aesthetic preferences
Efficient planning around our timeline and location
Fun activity suggestions that were (mostly) spot-on
Real-time adaptability for things like church service and brunch backup
Would we do it again? Absolutely, with maybe a little more manual vetting on location safety next time.
What’s Next?
This video wasn’t just for fun; we wanted to test how AI could be used creatively to plan real experiences, and it passed the test. If you’re curious about using AI tools to plan your content, travel, or production workflows, there’s plenty more to explore.
Want to build your own DIY studio setup like ours? Check out our Studio Blueprint Builder, an interactive tool that helps you pick the right gear and layout for your space.
And if you haven’t already, watch the full YouTube video for all the real-time laughs, gear tests, and surprises: Watch here
