Think AI sucks at planning holidays? You’re doing it wrong

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,” 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.”

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.

I concocted two fictional five-day trips tailored to the two cities I know best: Sao Paulo, Brazil, and New York. I planned to prompt three bots — ChatGPT, 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 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.

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 optimisation,” a fast-growing practice in which companies scramble to game the models so they appear in responses. (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. 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. 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).

Mollick urged 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 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. 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 uploaded advice from a “friend I trust who lives in Sao 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

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 uploaded my travel profile, I told each bot to ask me five follow-up 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. I said that sounded good, but just for one day. It suggested a trip to Pelham Bay Park and City Island in the Bronx — good advice if I am the target.

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.

For Sao 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. I assumed I could pare down each list by asking the bots further questions. That worked great, and at the end I asked to group the results into geographically sensible clusters.

Know what’s missing

Unlike you and me, AI does not 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’ access to 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 was created by Anthropic, does not. Microsoft’s Copilot has a deal with Nine Publishing, which includes The Sydney Morning Herald and The Age. 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.

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 am a fan of the food site Eater, which Claude and Gemini told me they could not search directly, while ChatGPT said it could. (It turns out Eater has a partnership with ChatGPT.) You can also double-check sources by asking the bot to cite the URLs it used to come up with the tips.

Sites that big-name chatbots can’t fully search sometimes offer their own AI bots. I tested Tripadvisor’s built-in assistant by asking it for advice about Sao Paulo hotels for under $150, and it did 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 was surprised when it recommended one restaurant and one place to hear live music that were no longer open, as any human user of Maps could have figured out. “You are 100 per cent correct,” the bot wrote after I called it out on the error, “and I completely deserve to be thoroughly benched on this planning session.”

My prompt also asked 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 was the Transamerica Prime International Plaza, but when I noticed it listed Expedia and Booking.com as its sources, I asked if it had also checked Google reviews. 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.

Claude made one blatant hallucination, recommending two traditional Brazilian bakeries “that haven’t gone gourmet”. But when I checked on Google Maps, the two places turned out to be a car park and a Japanese restaurant. ChatGPT didn’t make any mistakes that I caught, but that doesn’t mean there weren’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 found 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.)

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, but instead using them to nourish the bot and keep it honest, or at least as honest as a virtual assistant can be.

This article originally appeared in The New York Times.