The Bourbon Trail sounds nice because you're within a day's drive of ...
Nature...
The Blue Ridge Mountains
The Great Smokey Mountains
The Shenandoah Valley
Great cities and towns...
Savannah, Georgia
Charleston, South Carolina
Memphis, Tennessee
Google any of these for more info.
A word on Memphis though ... it has some of the worst poverty and crime in America, but it does have some very real charm and personality. You'll probably want to stop off a Beale Street, although it is a bit touristy, as it's the main stop in the city complete with BBQ joints and Blues bars. BB King has his own restaurant and blues bar (and toursity merchandise shop 😊 on Beale Street. But driving at night without knowing what you're doing you can find yourself in some rather scary neighborhoods with not much in the way of hotel rooms or accommodation. You might want to stick to downtown when looking for sleeping accommodation.
Also, given that you seem to enjoy booze and music 😊, I would highly recommend New Orleans, which you can probably get to within a day's drive of Memphis. I know some might have trepidation of visiting there after Katrina, but the city is alive and kicking, and it's still one of the most uniquely fun and charming cities in America. A great music city (birthplace of jazz afterall) and party city. I went just months after the Hurricane and the city center and tourist parts were up and running full steam. If anything, the hurricane aftermath has made it a cheaper and less crowded tourist destination.
As for the rest of America ... well, the Northeast is nice because you don't really need a automobile. You can take trains to/from New York City, Boston, Philadelphia, Washington DC, and all have good mass transit.
American culture is built around the automobile, for better or worse, and really the best way to experience America is through one. I would personally bypass any notions of a Jack Kerouac inspired coast to coast car trip across America as it's a big country and renting a car is going to be expensive, you'll just drive through American Suburbia Wasteland of Strip-Mall after Strip-Mall (I say this as a proud American). There are some great cities in America's middle, Chicago and Austin Texas. These cities are are worth seeing but not worth going GOING to see, if you catch my drift. My advice? After you're done on the East Coast and ready to go to the West Coast (to get to Ventura), fly on Southwest Airlines (the closest America has to Ryanair or EasyJet) to Burbank California. This is a suburb of Los Angeles and the best way to get to Ventura. From Ventura you're within half a day's drive of San Diego (America's most beautiful warm weather city, IMHO). And the Grand Canyon (One of the one things in America not only worth seeing, but worth GOING to see). But I highly advise driving up Califonia Highway 1. It's widely considered the most beautiful drive in America, hugging the Pacific Coastline (Google Images for examples of the scenery). From Los Angeles you can this route straight north into San Francisco, which is maybe my favorite American city (and you can take a day trip trip into the Redwood Forrests). From San Francisco you can take 101 through the Pacific Northwest into Seattle (which you can then ferry into Victoria Island, British Colombia Canada). If you've ever been inspired by pictures of New Zealand, you'll find very similar scenery in The Pacific Northwest of America and Canada (especially Canada). And as a drinker, America (rightly) is made fun of for their awful mainstream domestic beers, but they also have a lot of smaller breweries that make great microbrew specialty beers, and the Pacific Northwest is at the epicenter of this movement.
One bit of advice, many rental car companies in America have regulations about returning rental cars outside of the State you checked them out from. I'm not entirely sure what those regulations are, but it's worth investigating. It might be more cost effective to take cheap 1 way flights on the previously mentioned Southwest Airlines to cover long distances between cities across states (typically you can book ahead for as little as $99 one way, if you're flexible on dates and book ahead), and then rent a car when you arrive at your destination.
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