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?
asserted
it → find → Rome
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.
uncertain
most → replace → us
The problem: We’re not helping them enough.
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We → help → them
“They’re not oracles,” said Ethan Mollick, a professor who studies AI and its impact at the Wharton School of the University of Pennsylvania.
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who → ’re → Pennsylvania
Using advice from Mollick, other experts and tech-savvy friends, as well as tips from AI companies, I set out to test some theories about writing better prompts for travel planning.
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I → use → planning
I concocted two fictional five-day trips tailored to the two cities I know best: São Paulo, Brazil, and New York.
asserted
I → concoct → cities
I planned to prompt three bots — ChatGPT, Gemini and Claude — trying both the free and paid versions.
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I → plan → versions
(The paid versions tended to go deeper and work faster, and were less likely to run out of steam.)
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versions → tend → 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.
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I → go → years
I asked AI to advise a first-time traveller to São Paulo and a veteran New York City visitor who had already seen all the main sights.
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who → ask → 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.
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I → persuade → research
Here are some strategies that worked for me.
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that → work → 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.”
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who → pile → museums
Experts told me again and again, “Ask generic questions, and you’ll get generic answers.”
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you → tell → 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.
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they → end → responses
(It’s the AI equivalent of search engine optimization, which companies have used for years to rise to the top of Google searches.)
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companies → ’ → searches
That includes your specific tastes in travel, your goals for this trip and any advice you’ve already culled from friends or other sources.
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you → include → friends
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.
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you → compile → 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).
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Mine → include → Chinese
Mollick urged travellers to be honest, even blunt.
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Mollick → urge → travellers
No chatbot will judge you if you say your ideal Chicago trip favours hot dogs over haute cuisine (and neither will most Chicagoans, as long as you lay off the ketchup).
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you → judge → ketchup
In addition to your travel profile, you should feed the bot any other research you’ve done using your favourite sources of travel information or tips you’ve gotten from friends.
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you → feed → friends
The assistant will work those tips into your itinerary, or perhaps tell you why they don’t fit.
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they → work → you
For my São Paulo test, for example, I uploaded advice from a “friend I trust who lives in São Paulo.”
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who → upload → Paulo
(It was actually a document I shared with out-of-town guests who came to my wedding last year.)
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who → share → wedding
Ask the bot to help
AI can actually help you make your prompts more effective.
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prompts → ask → bot
Every step along the way, ask the bot if there is anything you can do to make your request clearer.
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request → ask → bot
For example, when I uploaded my travel profile, I told each bot to ask me five follow-up questions.
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I → upload → questions
For the New York trip, Gemini asked about my willingness to spend several hours travelling to a more distant but interesting part of the city.
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Gemini → ask → city
I said that sounded good, but just for one day.
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that → say → day
It suggested a trip to Pelham Bay Park and City Island in the Bronx — good advice if I am the target.
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I → suggest → Bronx
ChatGPT suggested Jackson Heights, Queens, saying it “feels almost mandatory for you.”
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it → suggest → you
That made sense, because it also happens to be the neighbourhood I lived in for more than 15 years.
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I → make → years
For São Paulo, instead of a day-by-day agenda, I asked for four separate lists — activities, restaurants, nightlife and lodging — with “too many” choices for each one.
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I → ask → one
I assumed I could pare down each list by asking the bots further questions.
uncertain
I → assume → questions
That worked great, and at the end I asked to group the results into geographically sensible clusters.
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I → work → clusters
Know what’s missing
Unlike you and me, AI does not have free rein on the internet.
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AI → know → internet
Many websites (including The New York Times, which has sued OpenAI, the maker of ChatGPT, and others for copyright infringement) block bots’ access to some or all of their content.
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which → include → content
Others have deals with specific AI companies.
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Others → have → companies
For example, ChatGPT and Gemini, which is owned by Google, have full access to Reddit — a great source for travel tips — while Claude, which was created by Anthropic, does not.
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which → own → Anthropic
…and 27 more, not listed.
The Aporia
