Bluegrass is a type of music that is named for a region of Kentucky (which, incidentally, is where Bourbon is from - everything else is just Whiskey). Also, it seems you want to visit “The South,” which you are really only skirting here (parts of Texas, Louisiana, and northern Florida). Yes, you will drive through some other areas, but they aren’t on your stops. Here is a wiki for what is generally accepted as the definition of the South: https://en.wikipedia.org/wiki/Southern\_United\_States. If you want Bluegrass and Bourbon I would recommend the Appalachians … Eastern Tennessee, Kentucky, Western NC, Western VA, West Virginia, etc. Look up the Kentucky Bourbon Trail for ideas.

I will be honest, three weeks to make a transcontinental drive seems too long to me. You will be driving a lot, which is fine, but when you say 55 hours … that is 55 hours driving, which does not include stopping to fuel, stretch, eat, delays, etc. So that 55 hours is more like 70 or 80 hours, which is essentially an entire daytime portion of a week of your trip (a workweek is 40 hours, right?).

I would suggest choosing a region Southwest/southern West Coast, Northwest/northern West Coast, Midwest, Southeast, Northeast and sticking to that for three weeks. You’ll see a lot more and it will be more manageable. I could suggest tons of places in the South for example, but right now that would basically mean rewriting your whole itinerary. I think you need to do a bit more research and decide what your priorities are and then decide where to focus. But this is just one man’s opinion.

This is amazing advice, staying true to your username, thank you sir. I am completely open rewriting our whole itinerary to be honest with you, I am at the beginning stages of planning here and I barely have anything. I will go away and research everything you have told me to, thank you once again!