This seems like it could be great to explore a new city, especially if you can randomize trips somewhat. Eg there's 4 options for a starting point, then 3 options for the next point, etc and when you get treasure-map, it's somewhat unique in that it randomly picked each spot.
We've looked into this somewhat as you could make basically make it a path finding problem.
The difficulty is creating the paths from A to B that feel worthy of being chosen e.g. taking a path that goes through quirky (potentially unmarked) alleyways, rather than going along the main road to the crossroad and turn left etc.
A lot of thought goes into choosing paths and locations that really set the scene, especially in the narrative based games!
Would to hear more thoughts on this though as it could be a nice pre-process to do and then refine
I hadn't thought about the path itself (I gave it legitimate 15 seconds of thought before commenting lol). It would be not fun to walk through an alley in an unfamiliar place to an unfamiliar location. Additionally, it'd be possible that the path itself is part of the experience if it's a neat way to walk like if there's a cool bridge or nice art.
If you have a sight that you want someone to walk by, I'd think that'd be a "walk though destination" and treat that like other points.