Don’t Let AI Plan Your Next Trip (Unless You’re a Fan of Chaos)

We’ve all seen the flashy headlines: “AI can plan your perfect vacation!” The promise of a flawless, personalized itinerary generated in seconds is tempting. But as a travel advisor, I’ve had a front-row seat to the reality, and let me tell you, it’s a mix of hilarious chaos and logistical nightmares.
Recently, a few clients in our initial connection call have presented itineraries they generated with AI, and the results were… let’s say “wild”. The AI’s suggestions were attempting to create an efficient travel plan but ended up instead with a marathon of impossibilities.
The AI Itinerary: A Recipe for Exhaustion

The core problem with AI-generated travel plans is that they live in a frictionless vacuum. They can tell you to visit the Louvre, then zip over to the Eiffel Tower, then hop on a train to Versailles, all within a few hours. They completely ignore the realities of travel. Here are just a few things it usually doesn’t consider:
- Lag time is a foreign concept – The AI doesn’t take into consideration the time it takes to deplane, get your luggage, navigate through an unfamiliar airport, nor account for the drive time (with traffic) to your hotel. The AI assumes you’ll instantly appear at your destination.
- Human needs are optional – Eating, sleeping, and, yes, even “pooping” are not factored in. An AI itinerary can be a relentless schedule of attractions with no built-in breaks.
- The aggressive pace is unrealistic – These itineraries are so packed that you’d spend more time traveling between places than actually enjoying them. You’d be racing from one landmark to the next, too exhausted to appreciate anything.
A Comedy of Errors and a “Whoops” Apology
I decided to test this out for myself and spent a significant amount of time prompting an AI to create a workable itinerary. It was a humbling and often comical experience.
After more than a dozen or so prompts, I thought I was getting somewhere. That’s when I noticed that the AI told me that March 29, 2026, was a Saturday. I knew it was a Sunday, so I corrected it. Its response was so perfectly robotic: “You are absolutely right! My apologies for the oversight. March 29, 2026, is indeed a Sunday.”
The lack of genuine understanding was truly highlighted when I asked it to shorten a trip to Germany. Instead of removing a day from the schedule, it just skipped a day entirely! March 31 was simply gone, as if we could all just fast-forward through time.
Also, keep in mind that because I am a travel expert, I knew that the AI was giving me incorrect information and timings between destinations. Others with less experience might only correct their AI a few times.
Now, I decided to try a similar routine with another AI which offered better results initially but when I tried to get it to change things around and eliminate a country, things got a little funky.
I had even told it to give me a more balanced itinerary but instead, it kept the first country short and gave all the dates eliminated from Germany to England.
It even decided to offer the impossible! I knew that travel to visit one sightseeing item was a full day trip (transportation alone took almost 8 hours of the day) but the AI thought it would be a good idea to take an evening train to Liverpool to spend the night. Again, it was just “wild”!
The Human Touch: Why Travel Agents Still Matter
So, am I worried about AI taking my job? Not in the slightest. An AI can generate a list of places to see, but it can’t create a truly amazing travel experience.
A good travel advisor does more than just book flights and hotels. We understand the rhythm of travel. We know that sometimes you need an extra day to recover from jet lag or just to wander a city without a plan. We know how to build in buffer time for unexpected delays and how to create a schedule that’s ambitious yet achievable.
We won’t lie to you about the day of the week and we won’t just skip a day of the week to solve a scheduling conflict. We’ll make sure your itinerary is based in reality, leaving you to focus on what matters: making incredible memories.
Have you ever used an AI to plan a trip? What was the craziest thing it came up with?
PS: Most of this blog post was created by an AI but it still needed a human touch to make it sound less robotic and to add more anecdotes. Organizing your ideas into a blog post? That is a good use for AI!
