I Let AI Plan My Vacation and It Was Actually Kind of Brilliant

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Here's How it Went

Via Glyptoteket 

The logistics? Chef's kiss. When it was pouring rain and the sky opened up, my kids started their descent into chaos, I typed: "It's pouring, kids are losing it. What now?"

Instantly: "Go to the Glyptoteket - it's beautiful, indoors, and has a café."

SOLD. It became one of our favorite stops. Warm, gorgeous, and they sold cake. AI understood the assignment.

Tivoli Gardens? AI told me exactly when to arrive for the lights to come on. It was RIGHT. For those few hours of cotton candy and carousel music, my digital assistant earned its travel-agent badge.

4 a.m. airport taxi? "Yes, they run at that hour."

And there it was - a car waiting in the dark like a punctual Danish miracle.

The robot delivered. 

Until it didn't.

The Confident Lies

Via alessandrobiascioli

Here's the thing about AI: it doesn't say "I think" or "maybe." It says "Of course!" with the confidence of someone who definitely knows where they're going.

Which is how we ended up searching for the Copenhagen Tech Museum that has never existed. At least not outside AI's imagination.

We spent actual minutes on Google Maps, thinking maybe it was renamed. Or invisible. Or we were collectively having a stroke.

Nope. AI just invented a museum. Like a tourist on their fifth espresso, it described things it WISHED were there.

Restaurant recommendations? Time travel roulette.

Half were closed. One had become a clothing boutique. Another was, according to Google Maps, "temporarily relocated to someone's apartment."

At one point, I gave up and let 7-Eleven feed us. Which, in Denmark, is surprisingly gourmet. Hot dogs. Pastries. Happiness. Sometimes the algorithm wins by accident.

When I Started Talking To It Like A Person

Somewhere between day two and the rainstorm that tried to drown Nyhavn, something weird happened.

I started TALKING to ChatGPT. Not typing - talking. Like, "Please stop suggesting castles. I said INDOOR activities."

I caught myself defending it when my partner complained. "Yeah, but it's LEARNING!" I said - about an algorithm that definitely wasn't.

That's the strange thing about traveling with AI: you start assigning it personality. It becomes that overconfident friend who always sounds sure, occasionally gets you lost, but somehow still makes the trip better.

It's like having a travel buddy who never gets tired, never needs coffee, and never admits they're wrong. Ever.

The Train To Malmö (A Confident Mistake)

Via Cristian Manieri

"Is the train to Malmö covered by our ticket?"

"Yes! Absolutely! Enjoy the journey!"

Narrator: It was, in fact, not covered by our ticket.

We discovered this mid-platform, surrounded by actual Swedes who'd clearly seen confused tourists make this mistake before.

But even there - EVEN THERE - after I corrected it, AI immediately pivoted: "My apologies! Here's the ticket office. Here's the price. Here's the train schedule."

It doesn't dwell. It doesn't get defensive. It just moves forward with unshakeable optimism.

I kind of respect that.

The Rain, The LEGO, The Miracle Pastry

Via any_tka 

The rain never stopped. But AI gave it structure.

When I needed something quick: "LEGO store on Strøget - perfect for kids." When we were cold and cranky: "Conditori La Glace for hot chocolate and cake."

That second one? LIFE-CHANGING. The hot chocolate was so good, I briefly forgave AI for the phantom Tech Museum.

That's the secret sauce. AI isn't great at originality, but it's INCREDIBLE at convenience.

It removes friction. It gives you something to do NOW instead of doom-scrolling through "Top 10 Things To Do in Copenhagen (2021 Edition)" written by someone who's never been to Copenhagen.

Malmö In The Gray

Via Efrem Efre 

Our final day was across the bridge in Malmö, Sweden - another AI suggestion.

It sounded romantic: "A charming Scandinavian city, just 35 minutes away!"

In reality: 35 minutes of gray skies, wet shoes, and one spectacularly good cinnamon roll.

But AI rescued the day with a café suggestion that actually existed and train schedules that were actually accurate.

By the time we headed home, soaked and exhausted, I realized something: The trip was SMOOTHER than it would've been without AI. Not perfect. But faster, lighter, far less stressful.

What AI Gets Right

Logistics. Timetables. Museum hours. Instant reroutes when plans explode.

Scenario thinking. Not just lists of things, but "if X happens, do Y."

Infinite patience. Never loses its cool even when you're typing in all caps from a wet park bench.

It's like having a tireless assistant who doesn't care how many times you change your mind or ask the same question three different ways because you weren't paying attention.

What It Can't Do

Read the room. Or the weather. It will cheerfully suggest outdoor activities while you're drowning.

Feel exhaustion. It doesn't know when you're tired and just need to sit somewhere warm and quiet.

Understand nuance. "Local experience" to AI means "Google's top three attractions," not "stumble into a random café and have the best hour of your trip."

It doesn't know when your kids have had enough. When you're craving silence. When the best memory will be an accidental detour, not a planned stop.

The Real Magic: Less Planning, More Living

Via Brady Knoll

AI didn't make the trip perfect. It made it POSSIBLE.

It freed me from the paralysis of choice - from comparing every restaurant, every museum, every train ticket option for three hours while accomplishing nothing. It turned planning into a conversation, not a chore.

For that, I'll forgive the nonexistent Tech Museum and the confident lies about train tickets.

Because when you're traveling with family in the rain, what you really need isn't flawless data. It's a friendly voice saying "Try this instead" without judgment or exhaustion.

Would I Do It Again?

Absolutely. But I'll still double-check everything, pack an umbrella, and keep 7-Eleven in my back pocket as emergency infrastructure.

AI can guide you. But you still have to live the story. And sometimes the best stories come from AI confidently sending you to museums that don't exist, then cheerfully redirecting you to a café that changes your life.

That's traveling with robots in 2025, baby. And I wouldn't have it any other way.

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