Has anyone used Apple Maps (on the Mac) for RoadTrip planning?

I would like to use Apple Maps to plan a road trip, but I don't see a way to drop multiple pins for multiple locations.  for example, I'd like to visit South Dakota, specifically, Custer and DeSmet, but I'd also like to visit Devil's Tower in Wyoming, the petrified forest which is close by, some caves, etc.  I would like to be able to set my starting point and drop some pins for points of interest and then figure out what else is around those points of interest (PINs) such as restaurants, hotels, historical sites, etc.  And finally be able to pull all this together so I can figure out the road trip.
Has anybody done this and if so would you be willing to share some tips?

I don't see a way to drop multiple pins for multiple locations
This can't be done with Maps at this time. The best you can do is amass a set of bookmarks that contain a maximum of one starting point and one ending point with no way to organize them beyond the order in which they were created. (A completely fruitless exercise in my experience.)
IMO, you're much better off creating maps with Google Maps, saving those maps, then accessing your saved maps through the Google Maps app (in its settings) on your iOS device or via the Web on a Mac. You can also use the Google Maps app in conjunction with the TripAdvisor app and even the OpenTable app to navigate to places to stay and eat anywhere in the country.
(Don't underestimate the value of paper maps for long road trips like this, either.)

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