My wife and I did our first Tesla road trip (FL to New England) in June 2016, in our 2016 Model AP1 S85 (265-mile range). Supercharger coverage was pretty good all the way up and down the east coast, but I planned our stops using https://www.evtripplanner.com, https://supercharge.info, and an old Supercharger Reviews thread in this forum. I kept track of my actual mileage between stops and charging time at each supercharger.
Our second road trip was about 15 months later, same itinerary (more or less) and the same car. There were a few more superchargers available than on the previous trip, but most of our supercharger stops were going to be the same as before, so I didn't do much planning.
We're about to do another road trip, the usual itinerary, but this time in a 2018 S100D with 335-mile range. There are a LOT more superchargers along the route than there were on our previous trip 2 years ago. Between the extra superchargers and extra range, I don't have to think about where to stop -- our bladders and stomachs will probably make the choice for us. :-) I don't expect the superchargers to be as uncrowded as they were 2 years ago, but I'm not worried about it either.
I'm just amazed at how easy road tripping in a Tesla has become (not to mention having AP to make the drive easier). I realize there are parts of the country where coverage isn't as good and you still need to plan a bit, but that will change. I know some of you long-time owners started doing road trips back when supercharger coverage was very limited, so you must be even more amazed by the changes over the years.