I have tried both Google's my maps and scribble maps and boy, it is a pain in the ass to just... make a map of an interesting route. With some waypoints and some connecting lines. it's not impossible, it's just so fussy that I say forget it. Is this always so bad? Is there a tool that everybody swears by? should I just give up on the idea that I should be able to do this on my phone?

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I’ve tried the same thing, using Google, and I never achieved it to any satisfaction.
For a route, are you talking about public roads, or are you on a bike?

I generally don't have issues with Google Maps (shhh - don't tell the boss), but I'm not sure how many stops you're talking about / publicness of the route / etc.