May 11, 2026
How to Actually Evaluate an AI Trip Planner
AI trip planners are easy to evaluate badly. You type in a destination, the app generates a polished multi-day itinerary with a map, and it looks impressively useful. What you haven't tested is whether the plan is any good for you, on your dates, with your actual interests — which is the only thing that matters. Most of the differentiation between trip planning tools is invisible in a five-minute trial. Here's how to find it. Test 1: Change the Dates Take the itinerary you just generated and





