I think you'll enjoy the trip. Keeneland can get very crowded on Saturday fyi. Definitely go in the morning at Keeneland. Tailgating is fun as well. Get a nice map and drive the back roads around Keeneland as it's beautiful Horse Country. Don't know about hotel availability, but Georgetown isn't far, and if it's all booked, check Northern Kentucky (just south of Cincinnati) as it's about an 80 minute drive. There's Equus Run Vinery close to Keeneland that's nice. Of course Bourbon, Woodford Reserve, Buffalo Trace, are not that far. If you didn't know, you can walk around the barn area at Keeneland, and that I think is awesome especially in the morning.
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