We did it a few years ago (got the tee-shirt).
My son was graduating high school in STL, so went there first, then drove to Louisville. We stayed at the Seelbach Hotel, which is an old school (almost 120 years old) hotel that is now a Hilton property (points!). Small rooms, but very nice. Great bourbon selection at the main bar, so have a drink or three and then go down to check out the Rathskeller. We ate at a place called Havana Rumba, which was a really a good tapas bar. If you are a baseball fan, the Louisville Slugger museum is just up the street from the Seelbach.
The next morning, we checked in at the Louisville tourist information center for maps, coupons, and got our bourbon trail passport. If you get the passport checked for all the distilleries on their list, you get a free tee shirt. Yeah, been there got the tee shirt, but hey, it's a pretty cool souvenir.
Then, you can just drive the route from distillery to distillery. Some are better than others, but they were all very informative on bourbon and had tastings (not free). Makers Mark was pretty cool as you could wax dip your own personal bottle. We stayed one night in Lexington at a mediocre HGI there, but it was no problem to complete the entire trail (and get the tee shirt) in three days.
The distilleries don't serve you enough to get you a DWI, BTW. I don't remember any awesome meals along the way, but nothing stands out as really terrible either
We finished up with a final night in Louisville at the Seelbach and had a great meal at Jack Fry's.
Overall, it was a very lovely week. Very scenic part of the world and some good bourbon to boot. If you are a bourbon fan, definitely worth a few days of your life.