Summary: I gave AI agents control over my weekend vacation plans—hotels, travel, food, attractions—and the outcome was strangely human. Some parts ran smooth. Some missed the point. And in the middle of it all, I asked myself: Are we ready to let machines drive discovery, or are we just offloading basic decision fatigue?
Letting the Machines Take Control—Well, Almost
There’s no shortage of tools promising to simplify travel. Aggregators, discount finders, itinerary planners—all built to shave hours off planning. But what happens when you give one of these tools the full job? That’s what I set out to test. I turned to an AI agent called Operator, accessible via ChatGPT Pro, and gave it one clean directive: “Plan me a budget-friendly weekend trip by train. Good cuisine and some art would be ideal.”
This wasn’t about finding a hotel or a train ticket. I wanted the whole weekend managed without getting bogged down in tabs and browser windows. The AI’s answer? Bruges or Paris. Both are hit-and-run accessible from London, thanks to Eurostar. Bruges won—quieter, artsier, cheaper. Or at least that was the idea.
Booking with an Agent That Never Sleeps
Operator handled the basics well. It found a decent hotel near the train station, booked tickets that respected my budget, and even confirmed times that let me avoid mad morning rushes. So far, so good. But travel isn’t about sterile logistics. It’s about flow. Context. Texture. That’s where the cracks showed up.
My itinerary? One day long. “Visit the Markt. See the Belfry. Try waffles.” Useful, but superficial. More like a travel brochure scraped into bullet points than a plan backed by intent or insight. When I arrived in Bruges, the AI couldn’t help with real-time things like which track my train would use, or how to navigate from one museum to another when Google Maps flaked out. It also didn’t know places close early or which street corners stay noisy past midnight.
The Better Brainpower Came from Elsewhere
Operator wasn’t alone in this test. Claude, another advanced AI, did better in curating experiences. Its itinerary spanned interests—painting, sculpture, architecture—and even offered offbeat cafés that weren’t flattened by influencers. Then there was MindTrip, a dedicated AI travel tool built for group planning. Its standout feature: it lets you co-plan with other people live. That made it easier to involve human inputs, which frankly brought more value than the AI’s default recommendations.
So what’s the takeaway? None of the AIs were reckless. They didn’t book anything obviously useless or drop the ball on safety. But they also didn’t think like travelers. They optimized screens, not moments. They filtered, but they didn’t judge quality the way a seasoned traveler does. And they offered “choice overload reduction,” not discovery. Honestly, their job wasn’t to inspire. It was to narrow down.
Helpful, But Not Smart—Yet
Letting AI run the show was a bit like letting a teenager file your taxes. They might get some of it right, but they miss the odd deduction and forget that credibility—whether with the IRS or a four-star trattoria owner—is built with intuition, not just instruction.
Still, there’s something important emerging here. AI tools reduce time spent ranking options. You don’t need to open twenty tabs to compare hotels or read thirty “Top 10 Things to Do in Bruges” posts. That alone is worth something. But once you arrive, the AI fades out. At best, it’s like a concierge with amnesia. At worst, it becomes noise that adds to decision stress instead of cutting it down.
The Bigger Question: Are We Handing Over Too Much?
If AI becomes the new “front door” to travel, what do we lose? Discovery gets streamlined into algorithmic assumptions. Spontaneity becomes an edge case. Sound familiar? It should. This is the same algorithmic deflation you find in your newsfeed, your shopping cart, your dating matches. Everything becomes “according to most people.”
So here's my question: If AI helps you avoid bad decisions, are you also giving up on great ones? And if you give the machine more control next time, will you trust it to learn taste—not just transactions?
That’s the tension. AI is great at filtering. It’s fast at narrowing. But it’s still guessing. It hasn’t traveled, eaten, felt weather in its bones. It hasn’t walked back from a late dinner in unfamiliar streets or discovered a side alley artist with no Instagram account. You have.
Would I Use It Again?
Yes—but as a sidekick. Let it do the grunt work. Let it mock up a plan or trim noise. But don’t let it own the weekend. Because right now, it’s far better at booking your train than telling you why you’d want to get on it in the first place.
If we’re going to travel smarter, let’s be clear-eyed about what "smart" means. Is it about fewer clicks? Or richer experiences? How do you define a “good” trip? Time saved—or time remembered?
That’s your call. But it’s one a machine still can’t make for you.
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Featured Image courtesy of Unsplash and Ling App (oFWFpbw_bfk)