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?
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 realise. The problem: we’re not helping them enough.
“They’re not oracles,” says 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.”
Using advice from Mollick, other experts and tech-savvy friends, as well as tips from AI companies, we set out to test some theories about writing better prompts for travel planning.
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I concoct two fictional five-day trips tailored to the two cities I know best — Sao Paulo, Brazil, and New York. I plan to prompt three bots — ChatGPT, Gemini and Claude — trying both the free and paid versions.
(The paid versions tend to go deeper and work faster, and are less likely to run out of steam.)
One twist: I go undercover, using new accounts or “temporary chats” so the bots don’t know I’ve lived in the two cities for years. I ask AI to advise a first-time traveller to Sao Paulo and a veteran New York City visitor who has already seen all the main sights.
I’m 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 work 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 tell 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 optimisation”, a fast-growing practice in which companies scramble to game the models so they appear inresponses. (It’s the AI equivalent of search engine optimisation, 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.
The Field Museum of Natural History in Chicago. Credit: JEFF HAYNES/AFP
Mine includes 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).
Mollick urges travellers to be honest, even blunt. 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 tomato sauce).
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. The assistant will work those tips into your itinerary, or perhaps tell you why they don’t fit.
For my Sao Paulo test, for example, I upload advice from a “friend I trust who lives in Sao Paulo”. (It is actually a document I shared with out-of-town guests who came to my wedding last year.)
Ask the bot to help
AI can actually help you make your prompts more effective. Every step along the way, ask the bot if there is anything you can do to make your request clearer.
For example, when I upload my travel profile, I tell each bot to ask me five follow-up questions. For the New York trip, Gemini asks about my willingness to spend several hours travelling to a more distant but interesting part of the city. I say that sounds good, but just for one day. It suggests a trip to Pelham Bay Park and City Island in the Bronx — good advice if I’m the target.
ChatGPT suggests Jackson Heights, Queens, saying it “feels almost mandatory for you”. That makes sense, because it also happens to be the neighbourhood I lived in for more than 15 years.
For Sao Paulo, instead of a day-by-day agenda, I ask for four separate lists — activities, restaurants, nightlife and lodging — with “too many” choices for each one. I assume I can pare down each list by asking the bots further questions. That works great, and at the end I ask to group the results into geographically sensible clusters.
Know what’s missing
Unlike you and me, AI doesn’t have free rein on the internet. Many websites (including The New York Times, which has sued OpenAI, the maker of ChatGPT, and others for copyright infringement) block bots’ accessto some or all of their content. Others have deals with specific AI 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 is created by Anthropic, does not. And bots can’t necessarily see every Tripadvisor review or the full content of many travel and food publications.
So even though bots work quickly and effectively, they have limited resources. Using one can be a bit like hiring a master chef who gets to shop only at 7-Eleven.
Classic New York apartment block near Tom’s Restaurant. Credit: Stephen Scourfield/The West Australian
How do you know if a bot can search your most trusted sources of information? Name a site you like and ask the bot if it has access. For example, I’m a fan of the food site Eater, which Claude and Gemini tell me they can’t search directly, while ChatGPT says it can. (It turns out Eater has a partnership with ChatGPT.) You can also double-check sources by asking the bot to cite the URLs it uses to come up with the tips.
Sites that big-name chatbots can’t fully search sometimes offer their own AI bots. I test Tripadvisor’s built-in assistant by asking it for advice about Sao Paulo hotels for under $150, and it does a decent job. Reddit also has a bot that allows you to mine its seemingly infinite well of travel recommendations.
Beware of hallucinations
Gemini trumpets its access to Google Maps information and user reviews, so I am surprised when it recommends one restaurant and one place to hear live music that are no longer open, as any human user of Maps could have figured out. “You are 100% correct,” the bot writes after I call it out on the error, “and I completely deserve to be thoroughly benched on this planning session.”
My prompt also asks for lodging recommendations, asking the bots to scan user reviews and avoid any hotels with a pattern of complaints of nearby construction noise, a perennial problem in Sao Paulo. One of Gemini’s three choices is the Transamerica Prime International Plaza, but when I notice it lists Expedia and Booking.com as its sources, I ask if it has also checked Google reviews. Apparently, it has not, because the bot does an about-face, responding, “Dozens of Google reviewers explicitly warn light sleepers to stay away”, noting that drilling and heavy machinery noise start early.
Claude makes one blatant hallucination, recommending two traditional Brazilian bakeries “that haven’t gone gourmet”. But when I check on Google Maps, the two places turn out to be a carpark and a Japanese restaurant. ChatGPT doesn’t make any mistakes that I catch, but that doesn’t mean there aren’t any. You should independently check every place you plan to visit.
Set up a dedicated travel chat
Unless you’re never going to travel again, save your work. I find the Projects feature on ChatGPT and Claude a useful way to have what amounts to a running conversation about leisure travel separate from whatever else you might be asking. It takes only a click or two to set up, and the bot can tell you how. (Gemini has no exact equivalent to Projects.)
Russ & Daughters restaurant in New York. Credit: Mat Hayward – stock.adobe.com
If you create a project, you can use it during the trip to fine-tune or make a last-minute change, and even provide post-trip feedback so the bot gives you better results next time.
Think of AI chatbots as very smart but fallible tools that work best with long, detailed input and lots of pushback. That does not mean abandoning your time-tested travel resources (oh, hi there), but instead using them to nourish the bot and keep it honest, or at least as honest as a virtual assistant can be.
