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Sipping in the South was born from a bold idea: that bourbon deserves more than a bus ride and a stamp on a map. We’re not part of the Kentucky Bourbon Trail™—and that’s by design. The “trail” isn’t a trail at all. It’s a marketing ploy, and it often skips over what matters most: soul, story, and real Southern hospitality.
We offer somethi
Sipping in the South was born from a bold idea: that bourbon deserves more than a bus ride and a stamp on a map. We’re not part of the Kentucky Bourbon Trail™—and that’s by design. The “trail” isn’t a trail at all. It’s a marketing ploy, and it often skips over what matters most: soul, story, and real Southern hospitality.
We offer something richer, more intimate, and far more real.
Our experiences blend the elegance and edge of the Roaring Twenties with the heart of Kentucky’s heritage. Yes, we take you to distilleries—but we also take you into the story behind them. Into private tasting rooms. Into historic homes. Into the company of the people who live this culture, not just bottle it.
And if you’re wondering how horses became part of this world—it’s more than mint juleps and fancy hats. Long before the Derby was a fashion event, horses and bourbon were the lifeblood of Kentucky. Distillers raised thoroughbreds. Horse farms bottled bourbon. And from backstretch bets to rickhouse deals, these two worlds have always moved in stride.
With Sipping in the South, you’re not just on a tour—you’re stepping into that story. Into a time when hospitality was an art form and every sip had a little scandal behind it.
The rich history of bourbon, the folklore and the crafsmanship behind each bottle, and the beauty woven through Kentucky's disilleries all resonate deeply. Its a passion that continues to shape a distinctive approach to celebrating and sharing the spirit of Louisville -- blending bourbon knowledge, distillery lore and a touch of "grannie
The rich history of bourbon, the folklore and the crafsmanship behind each bottle, and the beauty woven through Kentucky's disilleries all resonate deeply. Its a passion that continues to shape a distinctive approach to celebrating and sharing the spirit of Louisville -- blending bourbon knowledge, distillery lore and a touch of "grannie gossip" with a love for the Roaring Twenties and the elegance of Old Victorian charm. The result is a Trail Less Traveled: an Authentic Kentucky Bourbon tour experience!
Our professional bourbon guides create a one-of-a-kind tour, unforgettable experiences with genuine Southern hospitality. Our guides have a background in the industry - working at bourbon distilleries, bartenders, lifelong residents, or bourbon connoisseurs — we understand bourbon hospitality and the difference between a bourbon distil
Our professional bourbon guides create a one-of-a-kind tour, unforgettable experiences with genuine Southern hospitality. Our guides have a background in the industry - working at bourbon distilleries, bartenders, lifelong residents, or bourbon connoisseurs — we understand bourbon hospitality and the difference between a bourbon distillery and a whiskey distillery. You'll be planning your next trip with us before this one even ends. Come spend a weekend on the Trail Less Traveled in Bourbon Country. We’ll start as strangers but leave as friends.
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We provide concierge planning services, including personalized research, advance ticket purchasing, and coordination with trusted third-party service providers. Our role is to enhance your experience through expert planning and partnerships. All services provided by third parties, including transportation, operate independently and are subject to their own terms and conditions.
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