Route: Downtown Walking Food & History Tour, 4 to 5 tasting stops around courthouse square
Tip: Tours run afternoons Tuesday to Sunday; the Sunday departure meets at The Jockey on Cheapside instead of the Visitors Center.
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★ 4.3
The Distillery District tour from Bites of the Bluegrass eats through the James E. Pepper campus, mixing food and drink stops with bourbon-era history.
Tip: Book the calendar link ahead; Manchester Street stops involve gravel and warehouse floors, so wear flat shoes.
★ 4.4
Central Kentucky Tours runs an 8-hour Barrel to Bottle day from Lexington, following bourbon from the cooperage floor to Maker's Mark and Wilderness Trail.
Tip: Wednesday to Friday only, with hotel pickup from 08:00; admissions and tastings are included but lunch is not.
★ 4.2
Kentucky Bourbon Boys has driven private three-distillery bourbon days since 2011, with tastings, lunch and door-to-door pickup from Lexington lodging.
Tip: Everything is custom-quoted, so email the group size and wish-list distilleries; Sunday runs a brunch-and-bourbon route.
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