Summary: Letting AI agents plan a short-notice vacation sounds like either a bold experiment or a quick way to ruin a weekend. But I handed over the reins to digital assistants to see if they could pull it off. Turns out, they didn’t crash the trip—but they didn’t steer it without bumps, either.
Setting Clear Parameters from the Start
Most travel stress comes from decision overload. Flights, trains, hotels, restaurants, attractions—each comes with dozens of options and no time to vet them all before you lose the will to go anywhere. That’s where AI promised relief. Could I hand over the research while maintaining control of the big picture?
I set a firm brief for Operator, an AI travel tool bundled with ChatGPT Pro: find me an affordable weekend getaway reachable by train, ideally with good food and some art to wander through. No flights, no fussy transfers, no wild spending. Just something sane and semi-refreshing.
AI Moves Faster—Until It Doesn’t
Operator quickly triaged a list of rail-accessible destinations and pitched two options: Paris or Bruges. Smart. I’ve been to Paris lately, so Bruges it was. Operator opened a browser tab and locked into Eurostar train schedules, picking out a return ticket with a later Sunday departure. A small touch, but thoughtful—maximize daylight at the back end of a short trip.
But then came the friction. The browsing session timed out before I confirmed the bookings. When I restarted the process manually, prices had jumped. That small window of efficiency the AI gave me was gone. It saved me time, but the delay cost me more. What could it have done differently?
Adequate, Not Imaginative: Hotel Booking and Itinerary Building
Next up: accommodations. Operator skimmed Booking.com and centered on Martin’s Brugge—a highly reviewed 3-star hotel just steps from the city’s central square. Not risky or adventurous, but practical and well-placed. No complaints, though it took a while for the AI to land there. Watching the process, it didn’t so much “decide” as stumble onto consensus based on ratings and price.
My hopes were higher for the itinerary. That’s where a little creativity could save time. But Operator’s initial suggestions disappointed. It pulled together a basic day plan likely scraped from popular guidebook summaries. De Halve Maan brewery, Church of Our Lady, maybe a canal boat ride—standard fare with no timing, no depth, and no alternate paths based on mood or weather. I found little that made the AI’s planning feel… tailored.
Overlaying Human Intelligence Where AI Falls Short
So I brought in reinforcements: other AI agents like ChatGPT itself and Claude by Anthropic. They gave me more detailed itineraries, including hourly breakdowns. Still, I had to tweak them—replace redundant stops, adjust logistics, and factor in real-world walking times.
Their plans became useful inputs, not finished products. More like brainstorming partners than actual assistants. The kind that sees the puzzle but has a blurry view of the table.
During the Trip: Helpful—but Not Hands-Free
Once on the ground in Bruges, the agents bounced back into usefulness. I used them to decode local train schedules, find dinner spots that met my price/taste/location filters, and get quick history on museums. In the moment, they made my phone feel like a concierge service. Well, a slightly robotic concierge with no sense of context.
Example: the AI tried suggesting trains home at absurd hours—one had me at the station at 6:30 a.m. on a weekend. I had to veto several misjudged moments like that. You don’t send a human home groggy from vacation while praising your own efficiency. What was it optimizing for?
The Tradeoff: Direction without Discretion
Net value? The AI tools did save me effort. I didn’t spend hours researching train tickets. I didn’t go down reddit rabbit holes trying to decode which neighborhood offered the “real” Bruges. But I couldn’t leave them unsupervised.
They lack instinct and judgement—two things travelers rely on more than we notice. Knowing when to slow down. Knowing when to add a detour. Knowing that walking in a drizzle to a bakery at 4pm might be more “authentic” than whatever was planned two weeks earlier. You can’t yet codify that into code.
So… Would I Do It Again?
With tweaks, yes. The AI agents are decent travel interns. They’ll tee up travel choices and handle basic logistics. But think of them like semi-trained staff, not decision-makers. They don’t know your boundaries, your quirks, or your non-negotiables—until you spell them out.
That’s the real negotiation here: automation isn’t about removing people from the process. It just relocates where attention and decision-making take place. Instead of scouting hotels, you evaluate the scout.
Curious: What would make you trust an AI agent completely with your travel? Where would you say no? And what part of planning would you happily surrender tomorrow if the results matched your preferences?
AI won’t replace your instincts—but maybe it can borrow some of your time back. Use that time wisely.
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Featured Image courtesy of Unsplash and Ling App (oFWFpbw_bfk)
