I've done the trail(s), but based out of Louisville. Willett was pretty bare bones but really cool and one of my favorite brands. A couple of "musts" IMO:
- Maker's Mark--just for the stunning campus and unique tasting room (in a limestone cave). Good food on property as well.
- Buffalo Trace--great tour and too many top line iconic labels to list here
- Keeneland race track--just beautiful and what you would imagine Kentucky thoroughbred horse culture to look like. No admission or anything necessary, as long as it's not a race day you can just kind of wander the grounds.
- Castle and Key is reportedly another stunner--it was under renovation/construction last time i was there but is finished now. I've heard great things about that stop.
- Woodford also has a beautiful campus--but if you're going out of your way and can only do one, Makers is more bang for your buck.
I didn't love Heaven Hill--it's a stand alone, pretty generic tasting room in an area that looks more like an industrial park than bourbon country, so unless you're a big fan of the HH labels I'd skip that. Agree that Scout & Scholar in Bardstown is a great stop for lunch or dinner.
It's a great trip and an easy one. We did several smaller distilleries and it can be fun to just kind of poke around without a plan if you have time.
Veteran tip: at some point you will get really tired of hearing the same canned info on the various distillery tours over and over and over: 51% corn, charred white oak barrels, at least 80 proof, etc. etc.
And again--I can't stress this enough--Maker's Mark. No better looking property in the entirety of Kentucky bourbon country.