Bourbon trail...

We did that exact trip last time the Breeder’s Cup was at Keeneland.

How many days are you setting aside for distillery tours? We did 2 1/2 days of tours and did 4, 4, and 2, so 10 total. Honestly, after 5 or 7 of them they all start to seem the same. This was 7 years ago so my info may be somewhat dated, but here are my rankings of them from best to worst.

1. Buffalo Trace
2. Maker’s Mark
3. Woodford Reserve
4. Four Roses
5. Willett
6. Wild Turkey
7. 1792/Old Barton
8. Jim Beam
9. Some new one(at the time)I’ve forgotten the name
10 Heaven Hill

Woodford, Buffalo Trace, Wild Turkey, and Four Roses are fairly close to Lexington if that is where you’re staying. The rest I listed are close to an hour away. I’d only do one of Jim Beam and Wild Turkey - they are very similar, and Jim Beam is kind of out of the way. Maker’s Mark is also kind of out of the way, but it’s a gorgeous property and their tour was very well done. Do NOT miss the drive into Woodford. When we went Four Roses had two locations - the distillery and the bottling facility. We skipped the bottling facility.

We didn’t stay in Lexington so I have no recs there.

One other tip. If you plan to buy bourbon there to bring home, prices are cheaper at the liquor store than at the distilleries. Some of them had distillery only releases - off hand, Maker’s Mark, Jim Beam, and I think Wild Turkey - but the core of their offerings were available at the liquor store connected to Kroger at much better pricing.

Also, there’s a place there that makes all the barrels for the distilleries and I think they give tours. I forget the name of the little town it’s in, but I want to say Lebanon. I thought that would be interesting but nobody in my group wanted to do it. We did drive by it one day.

Keeneland and was great. I know nothing about horse racing and a friend of a friend got us free general admission passes and passes to a tailgate outside the track. It was the year American Pharoah won the triple crown and was there. A lot of excitement around the track that day, then he won that race.

The Spleen's list is very good, here are 3 additional tours that I would highly recommend:

Bourbon 30 Unique Experience where you get to make your own blend from several barrels.
LINK

Independent Stave is the place The Spleen mentioned that makes barrels.
LINK /

Castle & Key rivals Maker's Mark in the beauty of the property, it was originally designed by Colonel E.H. Taylor, Jr.
LINK /

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Any advice on tours and great place to check out and dine around Lexington?

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We stayed at a bed and breakfast in Versailles called the Story Book Inn, we rented the cottage with my inlaws and my wife's sister and brother in law. Highly recommend that place if you don't have anywhere to stay yet

We ate dinner at Heirloom in Midway which was excellent.

We only ate lunch in Lexington, but it was incredible. We just happened upon a place called Corto Lima; tacos and Latin influenced food. The chef is a James Beard winner or finalist.

We ate lunch at a bar/grill in Frankfort that was pretty good called Goodwood Brewing

We ate dinner at the Kentucky Castle in Versailles...only place we ate I wouldn't recommend. It was decent but overpriced and the service was horrible.

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Buffalo Trace has a few different tours. The hard hat tour gets rave reviews, but it was completely booked when I tried to book it. We did the Architecture/History tour, which was pretty interesting. It was certainly different than the bourbon making process tours we did everywhere else.

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That may have been what we did too; my sister in law booked everything. Our guide basically just took us to his favorite spots, and it was mainly history/stories about the buildings and very little on the bourbon making process and we went into the little building where they bottle Blantons and a few other single barrels.