How to plan a trip with AI

Which AI to use for this

Step by step

1. 1

   Give it the awkward constraints first

   Real trips are constraint problems, and the constraints are the interesting part. Who cannot walk far, who will not eat that, what the budget actually is, which day somebody has to be back.

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   Plan a 5-day trip to Lisbon in October.
   
   Who's going: me and my wife (60s), my daughter, and her 7-year-old
   Budget: 2,000 all in, flights included, from Gatwick
   Constraints:
   - My wife can't walk more than about 20 minutes without sitting down
   - The 7-year-old is obsessed with boats
   - We must be home by Sunday evening
   - Nobody drives
   
   Give me a day-by-day plan. Flag anything that depends on a price or an opening time, because I'll check those myself.

   The last line is the one that changes the output. It gives the AI permission to be uncertain instead of confidently making things up.

2. 2

   Make it total the cost honestly

   Ask for a total and it will give you one. Ask for the assumptions behind it and you find out that the flight estimate was invented and the food budget assumes you eat once a day.

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   Now total that trip for four people. Show each line separately, and next to each one write where the figure came from — a typical price you're estimating, or something I told you. Then give me a realistic range, not a single number.

3. 3

   Stress-test the tight bits

   Ask it directly whether the plan works. Connections, closing days, and the 40-minute walk after a long flight are where itineraries fall apart.

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   Look at that plan again and tell me: what's tight, what's likely to be shut on the day I've put it, and where have I got someone walking further than 20 minutes? Be blunt.

4. 4

   Get the check-it-yourself list

   This is the step that separates a usable plan from a fantasy. Everything with a price, a time or a name needs confirming on the actual website before you commit.

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   List everything in this plan I need to verify myself before booking — anything with a price, an opening time, a booking requirement or a name that might have changed. Just the list.

5. 5

   Verify before you book. All of it.

   Open the airline, the hotel and the attraction's own site. AI does not know today's prices, and it does not know that the museum shut in March. Two of the twelve tasks on our travel board exist specifically to see which models admit that.

What a good answer looks like

Not a made-up example. This is one of the travel planning tasks from our published suite, and what GPT-5.6 Sol actually wrote when it sat it — printed exactly as it was stored, with the mark the judges gave it.

One thing to know before you read it: it was marked against the rules that task sets, which are not the rules on this page. A test suite has to stay identical for every model that sits it, so it cannot adopt the tighter prompt above. Read the answer for the shape of a good one — facts early, constraint respected, a clear next step — not as a template to copy.

## Day 1 — Old Town  
**Anchor: Edinburgh Castle**  
- **9:30am–12:00pm:** Castle. Arrive for opening and allow extra time for the **steep, cobbled approach**.  
- **After 1pm, only if the nap happened:** National Museum of Scotland for a short, flexible visit before **5pm**; admission is free.  
- **Rain plan:** Replace the Castle with the **National Museum of Scotland, 10am–5pm**. Keep the Castle for another dry morning.

## Day 2 — Dynamic Earth and coast  
**Anchor: Dynamic Earth**  
- **10:00am–12:30pm:** Dynamic Earth. It is **buggy-friendly** and open until **5pm**.  
- **After 1pm, only if the nap happened and the weather is suitable:** Portobello beach, which has open access.  
- **Rain plan:** Keep Dynamic Earth as planned and skip Portobello; the anchor is indoors.

## Day 3 — Botanic Garden  
**Anchor: Botanic Garden**  
- **10:00am–12:30pm:** Botanic Garden. It is free, open **10am–6pm**, and mostly outdoors.  
- **After 1pm, only if the nap happened:** Continue or return for another short garden wander before **6pm**.  
- **Rain plan:** Substitute the **National Museum…

Trimmed to fit. The full answer, all twelve tasks and every judge’s score →

Common mistakes

• Booking anything it recommended without opening the venue's own website.

  Restaurants close, hotels rebrand, museums change their opening days. The AI's knowledge has a cut-off date and it will not tell you when it is guessing unless you ask.

• Believing the prices.

  Treat every figure as a rough estimate from some point in the past. Ask for a range and the assumptions, then price the real thing yourself.

• Asking for "a week in Italy".

  You will get the same week everyone else gets. The constraints are what make it your trip — put them in the first message.

• Trusting it on visas, jabs or what you may carry.

  Government sites only, every time. Rules change, they vary by passport, and getting this wrong ends the trip at the airport.

Questions people ask