I pick a destination first and then look at maps for alternate routes to that destination. I normally don't fix waypoints because they get in the way of stops, possibilities for detours, exploring on foot, finding a nice place to stay even if it's mid-day, etc. Distance covered is of no particular interest unless I MUST get from A to B in a certain time frame.
I tried riding with others but found that I had to make too many consessions.
BTW, being retired really