I found this piece awhile ago and think it’s fascinating: Forget the Shortest Route Across a City; New Algorithm Finds the Most Beautiful from MIT Technology Review.
I would love to see algorithms and other such means to find the best a city has to offer. And it’s not all that far fetched. For a long time flickr.com had a feature that featured photos viewers found the most interesting. If something similar was available for cities, a whole new generation of flaneurs and happier tourists might result. It might even spur improvements to areas deemed less beautiful.