How to use ChatGPT to plan a trip

Trip length, who is coming, how much walking you want, the season, and one or two things you already know you want all change the answer. "5 days in Lisbon, two of us, slow mornings, one day trip, no museums before 11" returns something you can use, while "Plan Lisbon" returns a list you could have guessed yourself.

Ask for venue names and neighborhoods, in those words, because if you skip that you get categories: a traditional tavern, a nice lunch spot, a viewpoint. Those hand the research straight back to you, so the check is worth running: Montreal's planning page or Seoul's will tell you whether what came back is real.

A text itinerary cannot tell you that two of its Tuesday stops are forty minutes apart, and it cannot be shared with six people in a form that stays current. Paste the list into a mapping tool and the geography problems surface immediately, which is the same move as organizing any itinerary by day. Only the source of the list has changed, so the check is identical.

"Four days in Montreal in October, two of us, slow mornings, one day trip to a nearby town, no museums before 11. Named restaurants and neighborhoods, walking time between consecutive stops, and flag anything that needs a timed ticket." That prompt is enough, whereas "Plan Montreal" is a coin flip.

If you get categories back, ask again and insist on names, and then map them. A model that puts Old Montreal, the Plateau, and a market in the same morning has never done that walk, so the map will tell you in seconds.

ChatGPT will put a museum on its closed day and a dinner at a place that takes no walk-ins, because neither fact reaches it in a form it can trust. Treat every timed thing as unverified until you have opened the venue's own page. The expensive version of this is booking straight out of the chat: a table at a restaurant that moved last spring, or a hike that needs a permit nobody mentioned.

Keep the chat as research, and keep the trip in a map with addresses on it. Whether AI can plan a trip is the longer version of this warning, while this page is only the procedure.

One trick pays for itself: ask for walking time between consecutive stops, because models will happily produce those numbers and the wrong ones are easy to spot. A ten-minute walk that is really forty shows up as soon as you check two of them against a map.

Geography problems only appear on a map, because two Tuesday stops forty minutes apart read as perfectly reasonable in a paragraph. That is why the paste step is the part of this you should never skip.