18 Jul 2026

How to Plan a Trip With AI: My Exact 5-Day New York Itinerary

Learn how to plan a trip with AI, using a real five-day New York itinerary to cover flights, hotels, food, maps and day-by-day planning.

Every time I plan a trip I end up with fifty tabs open and no actual plan. AI fixed that for me.

I'm going to show you exactly how I'd use it to plan five days in New York. Pizza obsessive, good coffee every morning, a few of the viral spots I've been seeing everywhere, a Russian bathhouse, and somewhere decent to stay. Same process works for any trip. Just swap in your destination.

First: figure out where you're going

If you already know, skip this. If you're still at the "let's go somewhere" stage, this is the prompt that actually helps.

Help me choose where to go. Two of us, first week of October, flying from London, around £1,500 each. We want good food, walkable, a mix of culture and downtime, nothing more than a few hours on a plane. Not bothered about beaches. Give me five options that actually fit, with the honest downside of each. Tell me which you'd pick.

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