How to Use AI to Plan a Trip in 5 Minutes

Last month I planned a 5-day trip to Portugal using ChatGPT. Start to finish: 8 minutes.

I'm not saying it was perfect. I'm saying it gave me a solid starting point I could edit — instead of staring at a blank page for an hour.

Here's exactly how to do it.

Step 1: Give it the basics

Open ChatGPT and type something like this:

"I'm planning a 5-day trip to Lisbon, Portugal in September. I'm traveling with my partner. We love food, walking around neighborhoods, and local history. We're not big museum people. Can you give me a day-by-day itinerary?"

Hit enter. Watch it go.

Step 2: Ask follow-up questions

The first answer is just the start. Now you can get specific:

• "What neighborhood should we stay in?"
• "Give me your top 5 restaurant recommendations, not tourist traps"
• "What should we know about getting around?"
• "What's a day trip we could take from Lisbon?"

Each question gets you closer to a trip that actually fits you.

Step 3: Export and refine

Copy the itinerary into a Google Doc. Edit it. Move things around. Add notes.

You just did in 5 minutes what used to take hours of browser tabs and travel blogs.

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This is what AI is actually good at: taking a vague idea and giving you something concrete to work with. You're still making the decisions — you just have a really good assistant doing the first draft.

Want to practice this yourself? That's exactly what Day 3 of the challenge covers.