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Yes, I lived in Louisville once upon a time. Organizing your own itinerary is the way to go.
Visiting bourbon country’s different than vineyard tours/tasting in Sonoma or Napa, for example. There are comparatively fewer distilleries and the bottle shops won’t over serve you (pro or con - you decide) so you have the option for someone in your group to drive and still enjoy the experience.
Also, a good number of the big distilleries have a presence in downtown Louisville. It’s easy to hit multiple spots in a day if you’re walking/Ubering. Another reason you don’t need to do a tour.
I’m happy to answer questions about this + restaurants around Louisville. Otherwise, here are some of my favorite distilleries by location:
Louisville (aka Urban Bourbon Trail): Angel’s Envy, Old Forrester, Rabbit Hole, Michter’s, Stitzel-Weller
East Bourbon Trail: Woodford Reserve, Buffalo Trace, Wild Turkey, Wilderness Trail
South Bourbon Trail: Willett (my personal favorite), Maker’s Mark, Lux Row, Bardstown Bourbon
Bonus location: Proof is a restaurant in Louisville that has an extensive bourbon collection. When you’re sick of seeing how bourbon is made (hint: every distillery does it the same way), you can sit down at the bar here and try pours of rare stuff that you won’t find on shelves.
Pick the ones you want to go to and book in advance. Makers is a good tour/tasting. Bardstown has a great tasting room and has good food. Willet good food/bourbon. Lux is just ok.
Honestly book a tour, they help decide what are the best places plus provide the transport and ticket price is included
Make sure you book months in advance as they sell out quickly.
Ended up planning my own thing. Booked 2 a day (can prob fit one more but might be rushing). Faves were bardstown tour and the four roses tasting experience
Pro
I think the main thing to solve for is distance between distilleries. So depending on how long you’ll be there, one day you could do 2-3 tours around Loreto, and then another day 2-3 around Louisville etc. Typically tours will sell out a few weeks in advance, with the exception being Buffalo Trace that sells out the hour tours become available
I second proof, I love to grab a drink and explore their first floor museum
Definitely agree with booking distilleries early! Many of the tours are still limiting the number of people due to covid. We loved Willet, definitely eat there too. Another favorite we stumbled upon was Jeptha Creed. It was a nice spot for lunch (and cocktails) and the barrel house tasting was neat! We even got to bottle our own straight from the barrel and seal it up to take home! Definitely a different experience from the other distilleries.