I've been several times. I personally would not stay in Louisville - We stay in Lexington, Bardstown or Versailles. A majority of the distilleries are all within a 30 - 45 min drive of Lexington. There are a bunch of smaller craft distilleries that are cool, that aren't a part of the bourbon trail that you can hit up too around the same general area.
I preface to say that: it was a much better experience in 2013 & 2016. You could drive to any of the distilleries and pretty much grab a tour within the hour. Present day due to Covid and the explosion of "bourbon people", you will have to have reservations for tours. If you plan on taking tours, the most you are likely to be able to fit into a single day will be 2 -3. You will have to calculate the travel time from distillery to distillery, how long the tours last, time for meals etc... Most of the distilleries don't open until 9 or 10 and close by 4 or 5. So, getting all of your tour reservations to line up for a particular day is a pain in the ass. You can still visit the giftshops of the distilleries without taking an actual tour - some will allow you to just do a tasting that is separate from the tour.
The food at
Bardstown Bourbon Company was really good, and Willett gets rave reviews for their culinary experience, but it wasn't my cup of tea. (It is more of a fancy appetizer dishes, NOT a burger & fries or entre type of thing) The Old Fashioned was great though.
My Favorites for tours/scenery
Buffalo Trace
Wild Turkey
Woodford Reserve
Four Roses
Willett
Castle & Key
Jim Beam
Must Stops:
Keeneland - The grounds are open, and you can just wander around. If you get there early in the morning, you can watch them exercising the horses. It's beautiful (This goes over really well if you are taking a spousal unit
)
The Kentucky Castle - Amazing dining experience (They also have lodging if money isn't a concern)
A lot of places are still requiring masks, and the only one I know of that requires a vax card is Michter's in Louisville - so, I haven't been there. You can also go to Churchill Downs and walk around - at least it was when we were there. And then you'll wonder why the Kentucky Derby is held in that shithole (The TV makes it look a lot nicer than it is - Keeneland is 10X better, but they don't have the capacity that Churchill does.
In Lexington, the old
Distillery District is really cool. James Pepper Distillery is there, along with a damn good pizza joint and Ice Cream place (However, the Ice Cream place no longer gets my business - Check their facebook page for more info Crank & Boom) There's also an outdoor band area, and axe throwing place. Across the street is the Burl, an old dive bar that is 'semi-notorious'
Spend some time traveling on the
Scenic Blue Ridge Parkway Absolutely beautiful!
I'm sure others will add more info... That's what I got for now...I know I'm probably missing a lot!
Also, check out the Official Site
https://kybourbontrail.com/Oh, and check out
Shaker Village Really cool grounds, can go in all the buildings, has Shaker history..and the breakfast in the Inn was fantastic. They also offer Lodging (We stayed there one of the nights - Wife Loved it)