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Using AI To Plan A Trip Without Outsourcing The Judgement Calls

By Nigel Guy · 3 min read

Ask an AI tool to plan your holiday and it will produce a full itinerary in seconds — day one, day two, restaurant names, opening times, a tidy structure that looks like real research. It's tempting to just follow it. The trouble is that a plausible-sounding itinerary and a genuinely good one look identical until you're standing outside a restaurant that closed down two years ago, or discover the "must-see" viewpoint is a ninety-minute round trip that eats your only free afternoon.

The mechanism: the Draft/Verify/Decide pass

1. Draft. Ask for a rough shape — how many days per place, a sensible order given geography, a mix of activity types. This is where AI is genuinely fast and genuinely useful; it's good at structure.
2. Verify. Treat every specific claim as unverified until you check it: opening hours, whether a place still exists, whether a booking is actually required, current entry prices, visa or transit rules. AI models are trained on data with a cutoff and no live view of what changed since — check anything time-sensitive against a current source before you rely on it.
3. Decide. Once the shape is verified, the actual choices — which two of the five "highlights" you'll skip, whether you want a packed day or a slow one, whether the group actually wants the thing that looks good on paper — are judgement calls about your trip and your people, not research tasks. Make them yourself.

What AI is genuinely good at here

• Turning "we have five days and want a mix of city and coast" into a workable rough order.
• Generating options you hadn't thought of, to choose from rather than follow blindly.
• Translating and drafting — a polite message to a host, a packing list for a specific climate, a rough budget breakdown to sanity-check against.
• Reformatting a plan you've already made into something shareable with the people travelling with you.

What to skip

Skip trusting a generated itinerary's specific details — addresses, prices, hours, whether something requires a booking — without checking them against a current, live source; this is exactly the kind of time-sensitive information that goes stale. Skip letting the AI pick the trip's actual priorities; it doesn't know that one member of your group hates museums or that another gets travel-sick on long transfers. And skip over-planning a trip that would benefit from slack — a fully scheduled itinerary looks impressive and survives contact with reality badly.

Guardrails

• Anything AI tells you about opening hours, prices, current entry requirements, or whether a place still exists needs checking against a live source before you rely on it — this is exactly the sort of detail that changes faster than a general-purpose model's training data.
• Visa, vaccination, and border requirements change and vary by nationality; check these with an official source, not a chat tool, full stop.
• The itinerary is a draft for you to argue with, not a plan to follow silently. If it doesn't feel like your trip once you read it properly, that's the system working as intended — say so and ask for a different shape, or change it yourself.

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