Wardriving Route planning

[InertiaImpact]

Hi all,

I'm not having much luck looking for a tool for route planning.

I'd like an app of sorts that you can draw a box/whatever to indicate an area you would like to canvas and it would give you a route/navigation along any drivable roads in that area.
Something where I can look on this site and see"oh, this area isn't logged very well" and then draw that area in and go, rather than have to remember which roads I've taken and which way I need to turn at every intersection. (Especially in areas where the roads aren't in a grid.)

Thanks!