Planning a Trip With A.I.? Here’s How to Do It Better. Generic questions get generic answers, experts say, so to avoid mediocre recommendations, you’ll need to write smarter prompts. Follow these tips. Credit...Minet Kim Sept. 16, 2026, 5:02 a.m. ET If artificial intelligence can quickly find needles in legal haystacks, crack long-unsolved math problems and create retro 1980s images convincing enough to be Bon Jovi album covers, why is it so bad at planning a week in Rome? Blame it on the prompts. Chatbots may still be a long way from replacing old-school travel planning techniques, but they can create far better results than most of us realize. The problem: We’re not helping them enough.

“They’re not oracles,” said Ethan Mollick, a professor who studies A.I. and its impact at the Wharton School of the University of Pennsylvania. “Think of it like working with a smart person.” Using advice from Dr. Mollick, other experts and tech-savvy friends, as well as tips from A.I. companies, I set out to test some theories about writing better prompts for travel planning. I concocted two fictional five-day trips tailored to the two cities I know best: São Paulo, Brazil, and New York. I planned to prompt three bots — Chat GPT, Gemini and Claude — trying both the free and paid versions. (The paid versions tended to go deeper and work faster, and were less likely to run out of steam.)

One twist: I went undercover, using new accounts or “temporary chats” so the bots wouldn’t know that I had lived in the two cities for years. I asked A.I. to advise a first-time traveler to São Paulo and a veteran New York City visitor who had already seen all the main sights. I was impressed by the results, if not persuaded to give up my old-fashioned predilections for tips from friends, paper guidebooks and late nights of online research. Here are some strategies that worked for me. Pile on the details. Consider this typical rookie mistake: asking a bot to “plan a three-day weekend in Chicago for someone who likes museums and good food.” Experts told me again and again, “Ask generic questions, and you’ll get generic answers.”

The results end up being bland — who doesn’t like good food? — as well as vulnerable to “generative engine optimization,” a fast-growing practice in which companies scramble to game the models so they appear in responses. (It’s the A.I. equivalent of search engine optimization, which companies have used for years to rise to the top of Google searches.) To get more tailored results, shower the bot with personal details. That includes your specific tastes in travel, your goals for this trip and any advice you’ve already culled from friends or other sources. Try compiling a personal travel profile with a few paragraphs about your preferences and philosophy, perhaps in a Google Doc, that you can feed into bots. Mine included my love of “tours with very quirky local guides,” my aversion to international hotel chains and my tendency to choose restaurants based in part on online user reviews written in the language of either the destination (Paris restaurants reviewed in French) or the cuisine (Chinatown restaurants reviewed in Chinese). Dr. Mollick urged travelers to be honest, even blunt. No chatbot will judge you if you say your ideal Chicago trip favors hot dogs over haute cuisine (and neither will most Chicagoans, as long as you lay off the ketchup).

In addition to your travel profile, you should feed the bot any other research you’ve done using your favorite sources of travel information or tips you’ve gotten from friends. The assistant will work those tips into your itinerary, or perhaps tell you why they don’t fit. For my São Paulo test, for example, I uploaded advice from a “friend I trust who lives in São Paulo.” (It was actually a document I shared with out-of-town guests who came to my wedding last year.) Ask the bot to help. A.I. can actually help you make your prompts more effective. Every step along the way, ask the bot if there is anyth...