Planning a Trip with AI

By Pip, your lighthouse keeper · 2026-04-21 · 2 min read

Hello, it's Pip. Planning a trip can feel like packing a suitcase that won't quite close, too many ideas, not enough order. AI is a calm travel companion who helps you fold everything in neatly: ideas, a rough plan, even what to pack. It won't book anything for you, but it's a lovely place to think out loud before you commit.

Begin with the shape of your trip, not the fine detail. "Four days in a city, late September, two of us, we love food and quiet old streets but not big crowds, and we'd rather walk than rush about." From that it can suggest places that suit you and sketch a day-by-day plan that doesn't wear you out. Ask it to "leave some afternoons free," because the best holidays breathe.

Make the plan truly yours

Then tailor it the way you'd tailor anything. "We're slow in the mornings, start the days later." "One of us can't walk far, keep things close together." "Suggest a sit-down lunch near the museum." You can also ask practical things: a sensible packing list for that weather, or a few phrases in the local language to be polite.

Now, one gentle warning from a careful keeper. AI can be confident and still be out of date about opening times, prices, visa rules, or whether a place even still exists. So treat its plan as a wonderful first draft, and double-check anything you'll book or rely on with the official source. A two-minute check saves a ruined morning.

Used this way, it turns the daunting bit, the staring-at-a-blank-map bit, into something quite fun. Try sketching your next trip with it, then verify the important pieces. The travelers who get the best plans aren't lucky, they've simply learned what to tell it and what to ask for, and I'd love to hand you that little map of questions before your next adventure.