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Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour

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Overview

Available languages

English

Mobile ticket

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.

Additional Info

Public transportation options are available nearby

Not recommended for travelers with spinal injuries

Not recommended for pregnant travelers

Not recommended for travelers with poor cardiovascular health

Suitable for all physical fitness levels

Must be 21 yeas of Age

Not recommended for alcoholics

Cancellation Policy

All sales are final. No refund is available for cancellations.

What To Expect

1

Kentucky Bourbon Trail

Private 8 hour all-inclusive Bourbon Tour with up to 8 persons and 3 distilleries. This is a real bourbon experience! It’s perfect for beginners, couples or bourbon snobs. Kick off the tour with breakfast and bourbon in a historic Old Louisville Victorian. We set you up for success by teaching you the proper way to sip/nose, the difference between rye vs wheat, and a blind tasting of bottled-in-bond bourbons. Armed with this info we hit the trail with stops at 2-3 distilleries. The grand finale distillery is sipping from barrels with the owner and an opportunity to bottle your own and have it signed. Your super host will fill you in on the facts, and the juicy gossip of the industry. They will point out master distillers, 4th generations, and must purchase bottles. This tour is customized to your group’s personality. You chose distilleries from a list of east or south and we recommend the best of those to create a one-of-a-kind bourbon tour you’ll talk about for years to come.

8 hours • Admission Included

What‘s Included

Private transportation

Snacks / water

Tickets

picnic

Facts vs Fiction and everything in between

Expert Guide

Debbie Downers

Gratuity

Know it Alls

Options

Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour

Reviews

5.00

8 reviews

Total reviews and rating from Viator & Tripadvisor

8
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  • Bourbon Country on a whole different Level

    Uprison,,Nov 22, 2025

    - Review from Tripadvisor

    5.00

    We visit Kentucky every year and thought we’d done every bourbon tour, but meeting Angelique in line for the allocated release changed everything. She invited us to The Old Carter social club and created a customized experience for our group of seven that was personal, exclusive, and unforgettable. If you think you’ve seen bourbon country, spend a day with Angelique it’s on a whole different level.

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  • Truly Unparalleled Bourbon Tour/Guide

    Wander797516,,Nov 19, 2025

    - Review from Tripadvisor

    5.00

    Unparalleled tour of the bourbon trail for my father’s birthday with friends/fam of all ages, thanks mainly to our INCREDIBLE tour guide, Angelique. Angelique was a wealth of knowledge and did it all for us, tailoring our experience in real time based on what we wanted to do at that moment, and showing us so many cool nooks/crannies (and castles) we would’ve otherwise missed. She knew all the best food spots in the area and took food and coffee orders while we were on tours to have it ready when we returned, and would join us in the gift shop at each distillery to point out which bottles were collectibles/worth buying and which were ripoffs when asked. With her help, my dad came away with a $60 bottle of Old Fitzgerald that was priced online at $331 and a bunch of other bottles he was excited about. Vehicles were also first-class with AC and speakers to play our music. I’ve been on dozens of these kinds of tours in the past, but none like this so wanted to share.

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  • Seal Team Six Precision - hospitality was next level

    gmarybeth39,,Aug 10, 2024

    - Review from Tripadvisor

    5.00

    Angelique aka bourbon queen, QB1, time keeper, manager, coordinator, photographer, hype girl and myth buster was fantastic. Her and her team were dynomite. Leaned a lot, drank a lot, laughed a lot. The tiny details such as liquid IV and other hangover remedies made it over the top. At 1:30 we were all hungry and when we walked into Staxx the food was at the table, sandwiches cut in half for anll the share. We devoured it. The sausage and pork was the best. She took us to a couple of abandoned distilleries so you could get a real feel of what it was like back in the bootlegging day. We went to J Mattingly, Buffalo Trace, Woodford, Castle and Key and got a cocktail to go at Jeptha creed. She thought of everything. Even a blue tooth speaker for the whole bus. I can’t say enough about the details. The seal team six joke started at Woodford when we needed to be in and out in less than 10 mins…. 12 guys. We didn’t do so well at Jeptha but got much better by the end of the day. What made this tour so much fun was The silly fun all day long! Don’t forget your flask because it could be 90 mins before you do a tasting! Ha.

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  • VIP BABY!

    dainbarrelpick,,Nov 29, 2023

    - Review from Tripadvisor

    5.00

    Angelique and Tuwanna made our Kentucky bourbon trail experience amazing. The best tour company we’ve ever used on Viator. The personal breakfast touches at the Chateau on 6th were amazing and Old Louisville Whiskey Co was a great grand finale. Sitting with an owner and sipping from barrels was one of a kind. Thank you Ladies. The Tampa guys

  • Highly Recommend Angelique and Tuwanna

    davemD1250OV,,Nov 23, 2023

    - Review from Tripadvisor

    5.00

    The Marriott recommended We contacted Angelique, “she’s the best in the industry”. We were coming in for a football game and decided to stay the weekend for the bourbon trail. It was last minute and because she new everybody our group was able to have lunch at Jim Beam, and blend bourbon at Bardstown bourbon co including cigars around the fire pit. We stopped at several unplanned distilleries to see if they had any Kentucky only special bourbons. Tuwanna and Angelique were great. It was very impressive that they could get 8 persons into all these experiences, and keep us on track without feeling rushed. It flowed so perfect, I don’t think you could have planned any better. It’s hard to pick a favorite. The guys loved Old Louisville sipping from barrels with the owner. A great guy! Second day was just as fun as the first. We had brunch at the Chateau on 6th and sat in an Old Victorian parlor sipping on contrails and eating amazing food. The 2 hours flew by. It was sad to say goodbye. They all took great care of us and we will be back! I highly recommend this company for tours and you’ll want to be their friends.

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  • Impressive, you did the unexpected. The meal was outstanding. It is rare when a tour anticipates all of your needs with

    Ken N,,Nov 12, 2023

    - Review from Viator

    5.00

    Impressive, you did the unexpected. The meal was outstanding. It is rare when a tour anticipates all of your needs with out asking. Way to go.

  • Angelique we bow to your bourbon knowledge.

    300ashtonh,,Oct 21, 2023

    - Review from Tripadvisor

    5.00

    Our friends said to “call Angelique” ( he didn’t remember the name of her company) she’d take care of everything for you and gives you a real bourbon experience! It may be a little more but for that little bit more, you get so much more and he was right! Hail to the bourbon queen known as QB1. We had so much fun with her and her team. The bachelor party hung out with her “AfterParty” team who planned a super fun evening that lasted until the bars closed at 4:00am. We didn’t have to make any decisions, it was all right there in front of us. AMAZING. we’re coming back! This sounds crazy but even the little details like bourbon rescue kit filled with liquid IV, Tums, Tylenol, 5 hour energy…..hahaha.

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  • We were the outlaws with our inlaws!

    NelsonNeat,,Dec 12, 2022

    - Review from Tripadvisor

    5.00

    So much fun and the history is fascinating. Our guide Angelique is hysterical. She had all the answers and new everyone. Se kept us well hydrated and we drank some great bourbons and smoked some pappy infused cigars. We had so much fun we’re coming back in October for the Southern Experience.

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From US$3,200.00

5.00
(8 reviews)
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