Three itineraries that read better than they route.
These examples are intentionally awkward. The point is not that an AI would always produce them; it is that a text itinerary can hide a detour that becomes obvious once the stops are placed on a map.
Hakone sits much closer to Tokyo than Kyoto. Visiting Kyoto first and then returning east toward Hakone creates a clear geographic reversal before heading west again.
Stress-test this route →Florence is naturally between Rome and much of northern Italy. Jumping to Venice first and then dropping back to Florence adds unnecessary north-south movement.
Stress-test this route →Brussels lies between Paris and Amsterdam. Putting Amsterdam before Brussels creates a backtrack that is easy to miss when the cities are just a list.
Stress-test this route →The useful question is not “does the itinerary sound good?”
It is “what would I change before I start spending money?” RouteRiff is designed for that second pass: map the route, inspect the warnings, fix the order, then send a correction prompt back to the AI that created the original plan.
RouteRiff uses geographic and travel-load heuristics. It does not replace live train, road or flight routing. Verify real schedules and availability before booking.