Kentucky Bourbon Trail Exclusive Tasting Tour

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.
That’s where we come in.

We’re the local experts who take the trail less traveled, curating exclusive experiences with up to 5 handpicked distilleries. We book the best each one has to offer rare tastings, sipping straight from the barrel with the owner, blending your own bourbon, or mixing your own cocktail.

The Kentucky Bourbon Trail® is a nice start, but it’s not the whole story. It features a select group that pay to participate — but some of Kentucky’s best experiences aren’t even on their map.

We’re here to change that.

Every tour begins with our Private Bourbon 101 Social — a hands-on introduction to nosing and sipping that gives you the tools to truly enjoy what you’re tasting. Because when you understand bourbon, everything else gets better.

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

What's included:

• Tickets
• Cooler snacks water
• Picnic Lunch
• Transportation
• Expert Guide
• Experimental tasting
• Customized bourbon flight

Not included:

• Cigars
• Gratuity
• Know it Alls
• Debbie Downers

What to expect:

Duration: between 8 hours and 9 hours

Kentucky Bourbon Trail

, , Kentucky

Bourbon lovers should not miss the opportunity to visit the gritty city of Louisville during their stay in Kentucky. Venture from the bustling city of Louisville to the many world reknown Bourbon distilleries to learn how their spirits is made. Start with an interactive 101 bourbon social, teaching you the proper way to nose and sip, rye vs wheat differences and a one-of-a-kind sensory training experience. This private experience is a must to make your journey truly remarkable.

1 hour • Admission Ticket Included

J. Mattingly 1845 Distillery

20 Reilly Road, Frankfort, 40601, Kentucky

Private Blend your own Bourbon Experience complete with 2 bottles.

45 minutes • Admission Ticket Included

Woodford Reserve Distillery

7855 McCracken Pike, Welcome Center, Versailles, 40383-9781, Kentucky

A quick gift shop stop and self-guided tasting option

30 minutes

Castle & Key Distillery

4445 McCracken Pike, Frankfort, 40601-8233, Kentucky

A must do distillery to learn the real story behind Buffalo Trace distiller, E. H. Taylor Jr. and George T. Staggs. Scandalous! The grounds a gorgeous, great cocktails and food trucks. Sip away down by the river reminiscing of the days gone by when the train took them to the river for a day of picnicing.

45 minutes

Buffalo Trace Distillery

113 Great Buffalo Trce, , Frankfort, 40601-2091, Kentucky

guided tasting

2 hours • Admission Ticket Included

Whiskey Thief Distilling Co.

283 Crab Orchard Rd, Frankfort, 40601-9185, Kentucky

We end the day with a barn party... Drinking from barrels, tapping your foot to live music, the famous food truck, corn hole all around a campfire. Doesn't get more real Kentucky than this! Cowboy boots, hats and cigars welcome.

45 minutes • Admission Ticket Included