Why Your AI Trip Planner is Set Up to Fail You

In the travel world, AI is the newest "shiny object." My clients often ask if I use it, and some have even brought me itineraries they generated themselves to see if I can "fix" them. While AI is a fascinating tool for inspiration, there is a massive gap between a generated list of sights and a functional travel plan. Here is why relying solely on an algorithm can turn a dream vacation into a logistical nightmare.

AI Robot Plans Your Vacation

Three Reasons why AI Fails

1) The "Frictionless" Fallacy

AI operates in a world without physics or human biology. It can tell you to visit three museums in four hours, but it doesn't account for the "friction" of travel. It forgets the 90 minutes it takes to deplane, clear customs, and wait for luggage. It doesn't factor in the walk from the train station to the hotel. Most importantly, it ignores the "human" schedule—it doesn't leave time for meals, rest, or even basic bathroom breaks.

2) Digital "Hallucinations" vs. Real Dates

Accuracy is the backbone of travel planning. During my recent tests, I found that AI consistently "hallucinates" basic facts. I was told repeatedly by the AI that March 29, 2026, was a Saturday. When I corrected the AI, it apologized and then proceeded to solve a scheduling conflict by skipping March 31st entirely. In the world of AI, if the math doesn't work, it simply deletes time. In the real world, if you miss a day, you miss a flight, a reservation, or a non-refundable experience.

3) The Lack of Local Context

An algorithm can scrape data, but it doesn't have "boots on the ground" knowledge. It doesn't know that a specific street is under construction, that a museum is closed for a private event, or that a 2:00PM transfer in a specific city is impossible due to local traffic patterns.

My AI Experiments: A Comedy of Errors

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.

Background: A client wanted to visit 3 countries (Italy, Germany and England) in a short amount of time. I wanted to see if it was possible to do all three and if not, how to rework the itinerary to only visit two countries (Italy and England).

First Try

I asked the first AI more than a dozen or so prompts and I thought I was getting somewhere. However, this AI eventually told me a date was on a different day of the week. Then, it decided to remove a date entirely from the itinerary which is impossible!

Something to 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. I eventually got the AI to give me something I could work with.

Second Try

On my second attempt, I decided to try a similar routine with a different AI to see if it would generate better results. At first, it seemed more accurate but when I tried to get it to change things around and eliminate a country, things got a little funky.

I had told this second AI to give me a more balanced itinerary and remove the time in Germany. However, it kept the time spent in the first country very short and gave all the dates eliminated from Germany to England. That was not balanced at all!

It also 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 instead of spending the night at a hotel. Again, it was just “wild”!

The Bottom Line

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.

AI is great for brainstorming, but it cannot "hold a candle" to the nuanced work of a professional travel advisor. My job involves more than just picking destinations; it involves understanding the rhythm of a trip, managing the "human" elements of travel, and—crucially—knowing exactly what day of the week it is. I know how to build in buffer time for unexpected delays and how to create a schedule that’s ambitious yet achievable.

When you book with a human, you aren't just paying for a list of places to go. You are paying for a plan that is grounded in reality.

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! Using it to plan travel? Not so much.