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 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: São 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 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 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.) 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.
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.
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 traveling 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.
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. 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 São 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% correct,” the bot wrote after I called it out on the error, “and I completely deserve to be thoroughly benched on this planning session.” 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 parking lot 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.
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. — The New York Times
GRAPH POINTS
1. Write out your travel style, specific preferences, and philosophy to feed into the bot.
2. Feed the bot existing research you've already gathered from friends, guidebooks, or travel sites
3. Bots don't see the entire internet: Many publications and review sites block AI scrapers or have exclusive deals with specific platforms
4. Verify bot access: Ask the bot directly if it can search your favorite travel sites or request that it cite its sources with specific URLs
5. Always double-check details: Chatbots can confidently recommend permanently closed businesses or completely fabricate locations
6 .Cross-reference with real-world tools: Independently details on trusted mapping platforms or official websites before finalising your plans
Oman Observer is now on the WhatsApp channel. Click here
