One of the great advantages of being retired, as my wife and I are, is that you can grab unexpected deals when they show up, rather than taking whatever is available during the brief periods that you can get away from work. This was the case a few years ago when we took advantage of an incredible flight deal to Albany NY and participated in a summer family reunion in New England. So we keep a working list of places we'd generally like to go and just watch for sales and other 'mistakes'. We just saw one for a very specific set of flights to Nashville that were about 40% off the normal price, and also found a car rental that allowed us to pick up just off the airport while still returning it to the airport for, again, about 40% less than we would otherwise pay. Since one of the trips on our list was vaguely listed as 'St. Louis and the South', this seemed an offer we couldn't refuse.
Now with airline seats and car rental arranged, we're starting to fill in a rough itinerary. The outline we have so far has us spending a few days in Nashville at the end of the Memorial Day weekend, then heading for St. Louis via Land Between the Lakes and Cape Giradeau for a few days. Next we'd head east across southern Illinois (Mt. Vernon for some family history), spending a night somewhere along the Ohio River and then continuing to Mammoth Cave and Cumberland Gap National Historical Park to Bristol VA/TN and Asheville for more friends and family. From there, we'd spend a few days in the Great Smoky Mountains/Pigeon Forge area before heading down to Chattanooga and some Civil War History (my great-great-grandfather fought there) and finally returning to Nashville for the flight home.
The timing is not anywhere near cast in stone as yet other than the start/end dates which leave us 15 full days to wander through the above area. With our roughly mapped outline and general interests in history, scenic nature, stately homes and gardens, as well as good eclectic food, I am hoping that you all can provide some insights into sites not normally covered by the standard guide books.