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Holiday travel season is about to start, and most people will use AI on the road the way they use Google: one question at a time, each answer starting from zero.
There's a better way, and it takes about two minutes before you leave.
On our three-week trip through Italy this summer, I asked AI well over 500 questions. None of them felt like starting over, because I set the context once, at the beginning, instead of re-explaining it every time.
The setup is a six-question interview. Where you're going and for how long. How much walking you actually want. Who's traveling and what they won't eat. What matters most: food, history, scenery or a mix. Where you're staying and how you're getting around. And anything you already know you want to see.
After that, every question gets better. "What's good on this menu?" is answered knowing my wife doesn't eat seafood or lamb. "Build me the best day" comes back as a plan built around how much walking we wanted and the heat that afternoon, not a list of attractions.
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Where to run it so it sticks. Keep the whole trip in one place. Use one chat for the entire trip and keep coming back to it, or set up a Project in ChatGPT or Claude and paste your answers in once. Start a fresh chat every time and you're back to square one.
Three questions to try once it's set up:
"What's on this menu that we'd actually like?" with a photo of the menu.
"We have four free hours and it's 95 degrees. Build the best afternoon."
"Is this restaurant worth the walk, or is there something closer that fits us?"
Two rules worth adding.
Tell it not to invent opening hours or prices, and to say so when it isn't sure. Hours change, and a confident wrong answer costs you a closed door. The prompt has this built in.
Don't paste passport numbers, card numbers or booking confirmations into it. It doesn't need them to help.
Update it when plans change. Swapped cities, added a day, someone joined you? One sentence keeps every later answer on track.
By the second week in Italy, without repeating anything, it knew we kept ordering grilled veal chops and regional pasta, and it steered us toward exactly that kind of place without being asked. That's what two minutes of setup buys you.
On the site: the exact six-question prompt, word for word, and a quick before-and-after of what changes once you run it.
What job will you give ChatGPT first?
— Jerry
AI Super Simplified