How to get useful holiday plans from chatbots: practical prompting tactics

The useful part

"They're not oracles," said Ethan Mollick, a professor who studies AI and its impact at the Wharton School of the University of Pennsylvania. "Think of it like working with a smart person." Blame it on the prompts: AI can generate impressive travel advice when fed the right amount of intel. I planned to prompt three bots — ChatGPT, Gemini and Claude — trying both the free and paid versions.

How it works

• (It's the AI equivalent of search engine optimisation, which companies have used for years to rise to the top of Google searches.) Even though bots work quickly and effectively, they have limited resources.
• The assistant will work those tips into your itinerary, or perhaps tell you why they don't fit.
• For example, when I uploaded my travel profile, I told each bot to ask me five follow-up questions.
• That worked great, and at the end I asked to group the results into geographically sensible clusters.
• So even though bots work quickly and effectively, they have limited resources.

What to take from it

ChatGPT suggested Jackson Heights, Queens, saying it "feels almost mandatory for you." That made sense, because it also happens to be the neighbourhood I lived in for more than 15 years. Apparently, it had not, because the bot did an about-face, responding, "Dozens of Google reviewers explicitly warn light sleepers to stay away," noting that drilling and heavy machinery noise start early. You're doing it wrong Advertisement If artificial intelligence can quickly find needles in legal haystacks, crack long-unsolved maths 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?

Example or evidence

• Microsoft's Copilot has a deal with Nine Publishing, which includes The Sydney Morning Herald and The Age.
• 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 AI to advise a first-time traveller to Sao Paulo and a veteran New York City visitor who had already seen all the main sights.
• — as well as vulnerable to "generative engine optimisation," a fast-growing practice in which companies scramble to game the models so they appear in responses.

Details worth keeping

Pile on the details Advertisement 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? Using one can be a bit like hiring a master chef who gets to shop only at 7-Eleven. To get more tailored results, shower the bot with personal details.

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