AI is showing up in almost every travel conversation right now. Some people want it to plan their whole trip. Others do not trust it at all. After using it throughout a recent trip to France and the Netherlands, I think the answer is somewhere in the middle.
Creating itineraries for people is an exercise in listening.
I often think of myself as a travel therapist. My role is to listen, validate, coach, and guide. During intake calls with new clients, I try to ask enough probing questions to get to the heart of how people travel and what they actually need help with.
Do they want structure or freedom?
Do they want every dinner planned, or do they want room to wander?
Are they nervous about transportation?
Do they want history, food, scenery, comfort, adventure, or just fewer decisions?
That is the part of travel planning people often underestimate. The itinerary is the visible product. The listening is the real work.
So where does AI fit into this type of work?
How can AI actually enhance a trip?
As an early adopter of AI, I have spent a lot of time experimenting with it. Several years ago, I created a T-shirt shop almost entirely with AI. I did not make one sale, but I learned a lot.
Since then, AI has become much more useful. The recent ability of AI tools to search the internet, analyze information, and respond with more specific context has helped it find a real role in my business. But it probably is not where most people think it is.
Travelers are clearly curious about AI, but they are not completely sold on it. A 2025 YouGov survey found that only 30% of U.S. travelers said they were comfortable using AI for trip planning, while 40% said they were not comfortable. Another McKinsey survey found that fewer than one-third of travelers had used generative AI for travel-related tasks, but among those who had, 84% said it improved their experience.
That feels about right to me.
AI is useful. Sometimes very useful.
But useful is not the same as trustworthy.
I have had conversations with prospective clients about how they use AI as their travel planner. It is really good at gathering information and funneling it to the user. It can help explain a destination, compare neighborhoods, create a rough itinerary, summarize reviews, or even look at flight schedules.
But it still struggles with real-life execution.
Travel is not just information. Travel is timing, geography, energy, weather, crowds, restaurant hours, hotel location, transportation, personal preference, and the feeling you get when you are actually standing somewhere.
Would you trust a blind man to describe the Mona Lisa?
Maybe he could tell you what people usually say about it. Maybe he could explain the history. Maybe he could describe why people care about it.
But he still cannot see what is right in front of him.
That is how I think about AI and travel.
It can explain. It can organize. It can suggest. It can inspire.
But it cannot fully experience the place for you.
On a recent trip to Europe, I found myself really thinking about how AI could enhance my trip. I experimented with several prompts and exercises with interesting results.
Could AI create its own guide to the Rijksmuseum?
Could I use it to create a day filled with fun and adventure?
Should I trust its restaurant recommendations?
Could it help me understand a building, a painting, a neighborhood, or a random moment that caught my attention?
One phrase I keep seeing is that Gen Xers are using AI like Google. And honestly, that is probably true. But I think the more interesting question is not whether AI is better than Google.
The better question is this:
Can AI help turn random information into understanding?
That is where storytelling matters.
Humans do not really understand the world through isolated facts. We understand through story. We remember information better when it has a beginning, a setting, a character, a conflict, or some connection to something we already know.
That is why a good guide can make a city come alive.
A guide does not just point at a building and say, “This was built in 1642.” A good guide tells you who lived there, what was happening in the city at the time, why the building mattered, and how that one street corner connects to the larger story of the place.
That is also where AI can be helpful.
Not as the final authority.
Not as the thing that plans every minute of your trip.
But as a pocket guide that helps connect the dots when you are standing somewhere and want to understand more.
Here are some ways I used AI to enrich my experience.
AI helped me understand art, not just look at it
I have a baseline level of art history knowledge. I have been an art teacher and can recognize the difference between Romanesque and Baroque buildings. I can appreciate the difference between Van Gogh’s skill at blending color and the Flemish masters’ ability to capture authentic moments from the 1600s with such incredible realism.
But my knowledge is still surface level.
So how could I use AI in a museum to build my knowledge and make connections between things I already knew and new information?
One use for AI that I found really helpful was in art museums.
While walking through the Louvre and the Rijksmuseum, I found that the audio guide or app I was using often left me with more questions. It helped, but it did not always take me far enough. It gave me a few facts, but not always the larger story.
And when travel fog kicks in, that matters.
You can be standing in front of something extraordinary and still feel your brain start to drift.
So I used this prompt:
Act as an expert art historian. You specialize in the historical context and technique of the masters. When I send you a photo of a piece of art, describe the artist, the technique, and how this work fits into the historical framework of the region.
AI did a great job helping me go further than the short placard below the art.
It helped me understand not just what I was seeing, but why it mattered.
It helped me connect Dutch painting to trade, wealth, religion, politics, and the Dutch imperial period. It helped cement my understanding of how art reflected the economic and political structure of the time.
That is the important distinction.
AI was not just giving me more facts. It was helping me organize those facts into a story.
That story stayed with me as I walked back to my hotel.
Suddenly the canals, the houses, the art, the commerce, and the history felt connected. That is when travel gets good. You stop seeing things as separate attractions and start seeing the city as one big, layered story.
AI made hotel history more interesting
And speaking of hotels, if you are anything like me, you sometimes wonder who else has stayed in your room.
Or what the building was before the invention of a breakfast buffet.
Hotels that dig into their own history and help build context for the neighborhood do a great job helping guests understand where they are. They make the stay feel connected to the city instead of separate from it.
The Pulitzer Amsterdam does this really well. The hotel takes up a collection of historic canal houses and has converted them into a five-star hotel. Each room has a description of the history of the building and who lived there.
That got me thinking.
Will I meet a ghost tonight?
So I used AI to create ghost stories for hotel rooms, pubs, and taverns I visited.
Here was the prompt:
I want you to be an expert ghost storyteller. I am traveling through France and the Netherlands. I want you to use historical knowledge, death records, and news stories to write short ghost stories about the building I am staying in. To start, I’d like you to write a ghost story for the Frog & Rosbif in Paris, where I am drinking a beer currently.
Here is the beginning of what it produced:
“The Tap in the Wall”
“The first thing you notice about the Frog & Rosbif is that it feels like a pocket of London stitched into Paris, right there at 116 Rue Saint-Denis.
The second thing you notice, if you have been in Paris long enough, is that the street outside has a memory. Rue Saint-Denis has carried crowds, commerce, and darker trades for centuries.
You lift your beer and the glass is cold enough to bite. The pub’s lights shimmer in it, golden and alive. Foam gathers at the rim like a soft collar. You are halfway through a sip when you hear it, not a voice exactly, more like a sound with intention, a small insistence threaded between clinks and laughter.
A drip.
Not from the ceiling.
From inside the wall….”
And it got creepier…
“You glance at the seam again, and you notice something else: the faintest tremble, like a pulse. Not in the wall, in the air beside it. As if the building is breathing through a straw.
Rue Saint-Denis has been a stage for panic before. In 1832, cholera tore through Paris and killed tens of thousands, and the city learned how quickly a street can turn from lively to hunted.
And around this neighborhood, in the tight web of streets near rue Saint-Denis, people built barricades during the June Rebellion, when the city boiled over and the street itself became a weapon.
Later came the Paris Commune, and then “Bloody Week,” when fire and fury took monuments and buildings, and smoke rewrote the skyline.
A street like this does not forget. It just learns to hide its teeth.
Your fingertips hover closer to the seam. The wall is no longer simply cool. It is wet-cool, like stone that has been underground too long. The drip returns, steady now, a slow tap… tap… tap… like someone counting time with a single finger.
Tap.
Tap.
Tap….”
Now, would I publish that as verified history?
No.
That is one of the shortcomings of AI. It can take real historical context and blend it with imagination in a way that sounds very convincing. That can be fun, but it can also be dangerous if you forget what you are reading.
This is where you have to stay alert.
AI can create atmosphere. It can help you feel the age of a place. It can make you curious. But unless you verify the details, you should treat this kind of output as historical fiction, not documented fact.
Still, it worked.
It made a pub feel less random.
It turned a beer into a story.
It made me think about the street outside, the building I was sitting in, and all the lives that had passed through that neighborhood before I wandered in with a pint.
That is one of the best uses of AI in travel.
It can help a place feel less like a backdrop and more like a living story.
AI helped me get back out the door
One night in Amsterdam, I found myself back in my hotel room at 6 p.m. with no idea what to do next.
I wanted to go see things, but the museums were closed and I did not need another evening in a pub.
This is a very real travel moment.
You are tired. Your shoes are off. Your phone is in your hand. The room is comfortable. You start thinking maybe you are done for the night.
But I knew there was more city outside.
So I prompted AI with this:
Act as a street art expert. You know all the famous artists and have deep knowledge of the genre. You access countless sources when making analysis and locating specific pieces. Create a list with specific directions and coordinates for a scavenger-hunt-style project specifically for Amsterdam. Start and end the hunt from the Pulitzer Hotel.
This was more complicated, and it did not work completely.
That is another important lesson.
Street art changes. Murals disappear. Coordinates can be wrong. A piece that existed three years ago might be gone now. We also get lost and spending the moments looking down rather than looking up costs in the making memories currency. It is good at giving you a plan but doesn’t adjust well on the fly. AI can sound very confident while sending you toward something that no longer exists.
But the prompt still did something valuable.
It gave me a starting point.
It gave me motivation.
It gave me a reason to put my shoes back on and go see more.
And sometimes that is enough.
AI did not need to create the perfect route. It needed to create a story that got me moving.
Instead of “go walk around Amsterdam,” which sounds vague and easy to ignore, it gave me a mission: go find street art. Look more closely. Turn the city into a scavenger hunt.
That changed my attention.
And attention is really what travel is about.
You can walk the same street two different ways. One version is just transportation from point A to point B. The other version is a search. A story. A small adventure.
AI helped create that frame.
The real strength of AI is not information. It is connection.
This is where I think people misunderstand AI in travel.
The obvious use is to ask it for an itinerary.
“Plan me three days in Amsterdam.”
“Find me restaurants in Paris.”
“What should I do in London?”
Those prompts can be useful, but they are also risky. AI may give you the same basic suggestions everyone else gets. It may miss the nuance of where you are staying, how tired you are, what kind of traveler you are, or whether the information is still accurate.
The better use is more specific.
Ask it to explain what you are seeing.
Ask it to connect a painting to the history of the city.
Ask it to turn a neighborhood walk into a scavenger hunt.
Ask it to give you the story behind a building.
Ask it to help you notice.
Because travel is not improved by information alone.
We already have more information than we can process.
The magic happens when information becomes understanding.
And for humans, that usually happens through story.
A random date is forgettable.
A story about why that date mattered is memorable.
A building is just a building until you understand who lived there, what they feared, what they built, what they lost, or how their choices shaped the street you are walking on now.
A painting is just a painting until you understand the world that produced it.
That is where AI can be powerful.
It can help bridge the gap between seeing and understanding.
Where I still would not trust AI
Using AI for big things like building full itineraries is risky.
I would not blindly trust it with restaurant recommendations.
I would not trust it to know whether a small business is still open.
I would not trust it to understand whether a neighborhood is the right emotional fit for a client.
I would not trust it to build a complicated day involving timed tickets, transportation, dinner reservations, and real consequences if one part goes wrong.
AI can make things sound clean and easy.
Travel rarely is.
A closed restaurant is annoying. A bad hotel location can change the feel of an entire trip. A poorly timed transfer can create stress that carries into the next day. A missed detail on a once-in-a-lifetime trip is not just a bad answer. It becomes a real problem.
That is why I still believe human judgment matters.
AI can gather information.
A good travel advisor listens, filters, challenges, adjusts, and turns that information into a plan that fits the traveler.
Those are very different things.
My takeaway
After experimenting with AI in Europe, I would not call it my travel planner.
I would call it my pocket guide.
It was at its best when I used it to make a real experience more meaningful. It helped me understand art. It helped me imagine the history of old buildings. It gave me a reason to walk when I was tired. It helped connect random details into a larger story.
That is the sweet spot.
Do not hand your whole trip to AI.
But absolutely bring it with you.
Use it to ask better questions.
Use it to deepen what you are already seeing.
Use it to create small adventures.
Use it to turn information into understanding.
Just do not forget that travel still needs human judgment. It still needs taste. It still needs context. It still needs someone who can listen.
And if you would like the exact prompts I used in Europe, let me know. I am putting together a short list of AI travel prompts that can help enhance your next trip without letting the robot drive the bus.