THE DISPATCH
Make Your Next Trip Yours. Not Everyone’s.
Left to its defaults, AI plans the same trip for everyone. The questions you ask turn it into yours.
By Paul M. Rand, Founder and Editor
of Nomadic Spirit
Ask ChatGPT to plan a two-week trip in Italy, and it will give you a perfectly good trip. It also gave that trip to the hundred people who asked before you. Left alone, the tool reaches for the most written-about version of a place: the hotels with the marketing budgets and the restaurants every list already names. It feels personal because you typed the prompt. The output is the same.
Use it as a researcher
No better tool fixes this. The change is in what you ask the tool to do. Let it build the trip, then make it yours. Building is the part AI does well, and faster than you could: a workable two-week shape with the train times and the opening hours, in seconds. Making it yours is on you, and the tool will not do it unless you ask. A guide tells you where to go. A researcher hands you what is known and leaves the decision to you. You want the researcher.
This is the third and final part of a short series on AI and travel. The first two made the case for caution, what the tools get wrong, and why your itinerary comes back looking like everyone else’s. You can find both Issues 11 and 12 at mynomadicspirit.com. This one is about what they get right, and it shows up in two places: the planning and the hours you spend once you are there.
Before you go
Start with the build, then go to work on it. The first draft will be solid and generic, and the questions that close that gap are ones the tool will never think to ask itself.
Ask it to find the flaws in its own plan. The same tool that called the itinerary wonderful will, pressed for problems, tell you the Vatican needs more than forty minutes, and the day it gave to three hill towns is really a day for one.
Then make it specific. The tool defaults to the timeless version of a city, the one with the most photographs, so push it toward the day you will be there. Tell it you land in Florence on a Monday and ask what is closed and what the city does anyway. The Uffizi and the Accademia both close on Mondays, and the first draft will not warn you. Ask, and you get the Monday version, the churches and the climb to Piazzale Michelangelo, the morning worth having when the galleries are dark.
One more question earns its keep. “What would someone who has lived here twenty years cut from this, and what is missing entirely?” You will not get a local out of it. The plan still comes back less like everyone else’s. Use ChatGPT, Claude, or Gemini, where you can push back and forth. The dedicated planners like Mindtrip and Layla are quicker, but they give you less room to argue, and the arguing is the part that pays.
On the ground
Now the camera does the research, and the rest is knowing which tool to reach for.
See it. Photograph a dish, a monument, a plaque you cannot read, and send it to ChatGPT or Gemini with six words on the end: and why does it matter here. The first half names the thing. The second half gives you the story behind it.
Museums. Download Bloomberg Connects before you go. It is free, it covers more than a thousand institutions, including the Met, MoMA, and the Guggenheim, and it does the work of the rented audio guide you used to queue for.
Menus and signs. Google Lens reads them in real time. In East Asia, where Lens still struggles, Waygo works offline.
Conversation. Google Translate’s conversation mode does the job. Lay the phone flat and take turns. Apple Translate is built into newer iPhones, and Pocketalk is a dedicated device for travelers who would rather not hold up a phone at all.
When things go wrong. A closed museum or a missed connection needs current information. Perplexity is free and shows its sources, and the search modes in ChatGPT and Gemini do the same. The plain chatbot will tell you, with great confidence, what was true two years ago.
All of it works the same way. You hand the tool the questions with known answers: the transit time, the visa rule, the word on the menu, and the name of the thing in front of you. It hands you back the afternoon, the conversation you would have walked past, the dish you now know to order, and the reason it is on the table.
