The Trail Less Traveled - An Authentic Kentucky Bourbon 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

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.

From: $0.00

Location: Louisville

What's Included

Community Discussion

Q&A

Q: What's the age limit for this bourbon tour? Can my 20-year-old join?

A: Unfortunately, the legal drinking age in Kentucky is 21, so your 20-year-old won’t be able to participate in the tastings. However, they can still join the tour and enjoy the experience—just no sipping for them. You might want to keep that in mind when planning!

Q: Can we reschedule if the weather's bad? I don't want to miss this trip!

A: Yes, you can definitely reschedule! If they have to cancel due to severe weather, just reach out to them directly, and they’ll help you find another date. It’s great that they consider the safety of their guests.

Q: What should I wear for the bourbon tour? Is it casual or more upscale?

A: Casual is definitely the way to go! Most people wear comfortable clothes since you'll be moving around to different distilleries. But don't forget good shoes—some places can have uneven ground. Just dress in layers since the distilleries can vary in temperature.

Discussions

Thinking about gifting the Kentucky Bourbon Tour - any thoughts?

I’m considering booking The Trail Less Traveled bourbon tour for my husband’s birthday. He’s a huge bourbon fan, and this tour sounds amazing with the personalized tastings and meeting distillery owners. Has anyone done it? How was the experience? I want to make sure it’s worth the $$!

Just did the Trail Less Traveled tour—so good!

Honestly, I had the best time on this bourbon tour! The guides were super knowledgeable, and the tastings were incredible. We even got to blend our own bourbon, which was a cool twist! Plus, the lunch was delicious. If you're thinking about it as a gift, I say go for it!