Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour, Kentucky

Sipping in the South was born from a bold idea: bourbon deserves more than a bus ride, a stamp in a book, and a cookie-cutter, self-guided checklist.

We’re the local experts who take the trail less traveled, carefully curating intimate, exclusive experiences for mixed and novice groups. Pick your one must-visit distillery and we build the day around it, selecting the best each stop has to offer including a fun mixology class.

The Kentucky Bourbon Trail® is a great intro, but it’s only features a select group of distilleries that pay to be listed — but did you know, some of Kentucky’s best experiences aren’t even on their map!

We go beyond the map to hidden gems, private tastings and unforgettable moment including great food.

Every tour begins with our Bourbon 101 Social — a hands-on experience that teaches you how to nose and sip like a pro. Because when you understand bourbon, everything else gets better.

And yes — we even save 30 minutes for rare finds at local liquor stores.