You could do it with custom development work -- write your own iOS and/or Mac app that uses Apple's Maps API, but this becomes a fairly substantial software project that you need a programmer to create. It's not doable just using the Maps app on your device as a user.
Thanks for bringing this up, the guides feature needs a serious overhaul, the fact that I can’t even add a simple note other than the title of the guide annoys me on a weekly basis. Having to resort to notes is clunky :(