My VIP 3 Day Kentucky Bourbon Trail Tour Experience
~Steve Kempton
I’ve done the Bourbon Trail before, but my recent three-day trip (Feb 27, 28 and March 1, 2026) with Jon and Top-Tier Bourbon Tours was in a completely different league. We approached Jon with a specific request: a true VIP experience centered on artisanal and craft distilleries mixed with must-see mainstream stops. Jon took our vision and built a custom, high-end itinerary that exceeded every expectation.
From the moment we were picked up in a brand-new luxury sprinter van, it was clear this wasn’t just a tour. After a great burger at Mussels and Burger Bar, the tone was set. Jon’s deep-rooted connections and “insider” status really became apparent. We had reached out ahead of time to arrange a private barrel pick for a charity auction, and Jon’s refined palate was invaluable as he guided us toward a rare Single Barrel Double Oak Rye. He then coordinated the bottling of 216 bottles in under 48 hours so they were ready for us before we left—and he even provided secure, climate-controlled storage for our “precious cargo” overnight.
We ended that first day at Uncle Boojie’s for a signature “Holly” pour and cocktails. Sitting in their 1920s bar with the massive limestone fireplace was the perfect atmosphere for Jon to sit with us, outline the rest of our journey, and talk whiskey.
What makes Jon truly unique is that he is an endless pit of bourbon knowledge, and his hospitality continues well beyond the scheduled tour hours. After the first day of touring, he and Jarrod led us to the Louisville Thoroughbred Society for cigars and whiskey, even inviting the single barrel specialist from Peerless to join us to talk shop.
The second day started with an eye-opener pour of Jon’s favorite Willet Purple Top. He took us to “hidden gems” like Bluegrass Distillers and Dark Arts, where we found flavor profiles you just can’t find on a standard store shelf. Jon timed everything perfectly to avoid crowds, allowing for private tours and relaxed distillery bar hangouts. He even arranged for us to meet one of the owners at Bluegrass, and I ran into one of my favorite bourbon influencers at Dark Arts. That night, we hit the Trial and Error Speakeasy at Pursuit Spirits, where Jon sat with us, helping us navigate the menu and just talking about life outside of whiskey.
Jon was incredibly flexible throughout the experience. Whether it was finagling us into the Whistlepig Bank Vault just before closing or adding a last-minute private tour at Rabbit Hole, he made it happen. Even when we had to shift plans and miss the Evan Williams tour, he made a quick call to ensure the distillery held two cases of Old Fitzgerald 9 Year for our group to purchase at MSRP—a true insider move. He also knew exactly when to insist on certain stops, like the Stitzel-Weller Distillery, which is a true piece of bourbon history.
To top it all off, Jon brought us to Neat Bourbon Bar and Bottle Shop for what was easily one of the best stops of the trip. He personally guided us through vintage tastings of a 1992 Blanton’s, a 1994 Maker’s Mark, and the “holy grail”—a legendary Stitzel-Weller wheated bourbon from the 1970s. We finished the trip with drinks at Bardstown Bourbon Co. and a final recommendation at Green River Distillery: a cold brew special called “The Dude Imbibes.”
Jon starts the trip as your guide, but by the end, he feels like a member of the group. If you are looking for a curated journey through Kentucky with someone who has total command of the local scene, Jon is the only person to call. This was, without a doubt, one of the best trips of my adult life.
— Steve Kempton