GuardTrails
An AI assistant answers what it is asked. That is its strength, and also its limit: if the request does not contain the right questions, the answer will not deal with them. We use one ourselves, and that was the first thing we learnt.
Here are the seven questions to ask yourself before asking for an itinerary — from an assistant, an operator, or yourself. None is technical. All of them change the answer.
1. How many days does the content need?
Ask this before saying how many days you have. If you start with "I have three weeks", you will get a three-week trip, with arguments — not a view on what the destination requires.
Only then compare. And ask what each week removed would cost.
2. How many times will you repack?
This is the parameter that decides most about a long trip, and nobody asks it. On our trips we changed accommodation every day and a half, without ever choosing to.
Give a number: "no fewer than two nights per lodging", or "three". → Base-change tolerance · Eleven hotels in twenty nights
3. Beyond what temperature does your day stop?
Escaping heat is not a matter of latitude, it is a matter of ceiling. Ours is around twenty-four degrees: above it, we no longer walk in the afternoon.
Give yours, and ask for the programme to account for it hour by hour, not as a monthly average. → Temperature ceiling
4. What do you want to do, in proportion?
"Nature and culture" says nothing. "Two thirds nature, one third culture" says something — and lets you check the result. On our operator trips, a third of culture requested often became nearly half delivered.
Give a proportion, then count the city nights and nature nights in the answer.
5. Where do you want to breathe?
On a trip longer than ten days, you need days with no plan — in the middle, never at the end, and never two in a row. Otherwise they happen anyway, on a good day wasted.
Ask for them explicitly, and say where they should fall. → Day with no plan · Where to put it
6. Which repetitions do you accept?
Three medieval towns in one day are not three experiences. But if beaches are what you came for, two beaches are not one too many.
Say what you accept to see several times, and what you want to see once. → Register saturation
7. What are you willing to give up?
Every trip gives something up. A programme that claims to do everything is wrong somewhere. Ask what the proposed itinerary leaves out, and why.
A template request, to copy
I am planning a trip to [destination] in [month], for [number] people including [children?].
First, tell me how many days this content needs, and what each week less would cost.
My constraints: no fewer than [2] nights per lodging; my heat ceiling is [24 °C]; I want about [two thirds nature, one third culture]; plan a day with no plan around the middle, never at the end; I accept repeating [beaches], not [medieval towns].
For each variant, say what it gives up.
Invent no driving time and no timetable: tell me what I need to check myself.
Once you have the answer
The best-framed request does not replace checking. The seven checks to do before you go, each drawn from a real case: How to check an itinerary planned with ChatGPT.
You can also send us the itinerary: we review it for free. Or let our engine ask these questions for you: that is exactly what it does — early access.
What we don't know
The example figures — two nights, twenty-four degrees, two thirds nature — are parameters of the engine, set per traveller, not rules. Replace them with yours: that is the whole point.
A missing question that changed your trip? Tell us.