Dots' family trip plan missed the practical details
He used ChatGPT Dots to plan a family trip to Tasmania: a road trip with his wife first, with some camping, and then meeting up with family who would fly in later. He says Dots was pretty bad at recommending options and didn't think through how practical they were. He ended up using its plan only as a starting point and built a better structure himself. His view is that you can't rely fully on an agent for a trip yet, especially if you're an experienced traveler. Trips with two groups arriving at different times are hard because every piece depends on the others, so give the agent your fixed dates, drive times you can live with and where everyone meets, and ask it to check the plan against those before it suggests anything.
The lesson: For multi-part trips, give the agent your fixed constraints and make it check each suggestion against them.
Copy this prompt
Plan a trip in two parts. Part 1: [NUMBER] days, two adults, road trip from [START] with [CAMPING NIGHTS] nights camping. Part 2: meet family flying into [AIRPORT] on [DATE] for [NUMBER] days. Fixed rules: no more than [HOURS] of driving a day, campsites must be bookable, and we must reach [MEETING PLACE] by [TIME]. Give me a day-by-day plan with drive times. Then check each day against my rules and flag anything that breaks one, before suggesting extras.
Our own prompt, written from what the source describes. We haven't run it ourselves. Text in [BRACKETS] is what you replace.
Watch out for
- Check drive times and campsite bookings yourself. Agents can suggest places that are closed, full or too far apart.
- Use the agent's plan as a draft, as he did, and fix the order of stops yourself.
Where this comes from
Original post by @sahil_harriram on X, Nov 2, 2026. We rewrote it in our own words. Check the original for the full context.
Read the originalWant to do this yourself?
Our guide compares which agents can do this job, with steps and a prompt.
Plan a trip with an AI agent: flights, a hotel and a budget
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