Planning
Using AI to plan a trip: what it is good at, and where it still gets things wrong
AI is very good at structuring a trip and unreliable about the facts inside it. Knowing which is which turns it from a gimmick into the most useful planning tool you have.
Asking a chatbot to plan your holiday produces something impressive in about eight seconds: a day-by-day itinerary, neatly formatted, confident, with times. It is genuinely useful. It also, reliably, contains at least one restaurant that closed two years ago and one walk that is four times longer than stated.
Both of those things are true at once, and the reason is the same. A language model is excellent at structure - the shape of a good day, the sensible order of things, the fact that you should not schedule two museums back to back - and unreliable about specific, current facts, because it is producing plausible text rather than looking anything up.
Use it for the first thing. Verify the second.
What AI is genuinely good at
- Sequencing. Given a list of things you want to do, it will order them sensibly by geography and time of day, which is the tedious part of planning and the part people get wrong.
- Adapting a plan to constraints. "The same three days but with a four-year-old and no more than an hour of walking per day" is a genuinely hard rewrite that it handles well.
- Being asked for less. "Give me one thing to do on Tuesday afternoon near Alfama" gets a better answer than "plan my trip", because the smaller the scope the less there is to invent.
- Explaining trade-offs. Ask why it chose one area over another and the reasoning is usually sound, even when a specific recommendation inside it is not.
The four failure modes to check for
Places that no longer exist
The most common and most costly error. Any restaurant, bar or venue in an AI itinerary needs one search to confirm it is open before it goes in your plan.
Confident wrong hours
Opening times and closing days are exactly the kind of specific fact models get wrong, and Monday closures ruin more days than anything else on this list.
Distances that do not survive a map
"A short walk" between two points can mean forty minutes uphill. Check the two longest hops of any day against a real map.
The generic top ten
Ask for a plan without saying who it is for and you will get the same plan everyone gets - the famous things, in a reasonable order, with nothing in it that is actually for you.
How to prompt it so the answer is worth having
The quality of an AI itinerary tracks almost entirely with how much of your actual situation you put into the question. Most people give it a city and a number of days, which is not enough information to produce anything but the average answer.
Give it, at minimum: who is going, what the occasion is, your pace, your budget, and one thing you specifically do not want. That last one does more work than anything else - "nothing that needs booking three weeks ahead" or "no long walks" or "we have done all the obvious things before" is what moves it off the generic list.
Then ask it to justify each choice in one line. It is much harder to invent a plausible reason for a specific place than to invent the place, so the reasoning column is a surprisingly good lie detector.
The structural problem nobody prompts their way out of
There is a limit to how much of this is a prompting problem. A general-purpose chatbot has no live connection to whether a place is open tonight, whether it takes bookings, whether it has a table at 8pm, or whether it is any good now rather than when its training data was assembled. You can ask better questions; you cannot ask it to know something it does not have.
That gap - between a model that understands what a good evening looks like and a model that knows what is actually available tonight - is the entire reason Planie exists.
How Planie approaches it differently
Planie starts from the same place a good prompt does: the occasion, the group, the vibe, the moment. The difference is what it plans with. Venues on Planie are real listings, reviewed by a person before they go live, with their own hours, price range and occasions attached - so the plan you get is built from things that exist and are open, not from things the model remembers.
It also means a place appears in your plan because it fits, not because someone paid for it to be there. Partners can raise their visibility, but no budget puts a venue into a plan it does not belong in. You can read exactly how that works on our placements page.
The app is not out yet. Join the waitlist and you will get one email, the day it is. For the method a good prompt is imitating, start with how to plan a date night in London.
Common questions
Is AI good at planning trips?
It is good at the structure of a trip - sequencing, pacing, adapting a plan to constraints - and unreliable about specific current facts like opening hours, whether a venue still exists, and real walking distances. Use it for the shape and verify the details.
What is the best way to prompt AI for a travel itinerary?
Include who is travelling, the occasion, your pace, your budget, and one specific thing you do not want. Then ask it to give a one-line reason for each choice - the reasoning is easier to sanity-check than the recommendations themselves.
Why do AI itineraries recommend places that have closed?
A general-purpose language model generates plausible text from training data rather than looking up live information. It has no way to know whether a restaurant closed after that data was assembled, so it recommends it with the same confidence as anything else.
Stop planning it. Let Planie do this bit.
Describe the evening or the trip you want and Planie builds the plan - real places, right area, open when you need them. It is not out yet.