Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Non-refundable booking. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 8 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour worth booking?
Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour is a 8-hour experience in Louisville, United States, from $3200 per person. It scores 48 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 8 reviews. This booking is non-refundable, so pick your date carefully. Same-day spots are currently showing.
- Outty Ranking
- 48 / 100
- Rating
- 5/5 (8)
- Duration
- 8 hours
- From
- $3200 per person
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 c
What you get
About this experience
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.
What's included
Included
- Private transportation
- Tickets
- Lunch
- Facts vs Fiction and everything in between
- Expert Guide
- Snacks / water
Not included
- Debbie Downers
- Gratuity
- Know it Alls
What you'll see and do
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.
480 minutes here · Admission included
Where it starts and ends
Meeting point
Louisville
Meeting point
Louisville
Meeting point
Louisville
Meeting point
Louisville
Meeting point
Louisville
Meeting point
Louisville
Meeting point
Louisville
Kentucky Bourbon Trail Welcome Center
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Returns to the starting point
Ends at
Returns to the starting point
Ends at
Returns to the starting point
Ends at
Returns to the starting point
Ends at
Returns to the starting point
Ends at
Returns to the starting point
Ends at
Kentucky Bourbon Trail Welcome Center
Before you book
- Cancellation
- All sales are final. No refund is available for cancellations.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Wed, Thu, Fri, Sat, Sun
- Group size
- Up to 8 travelers per booking
- Operated by
- Rison Ready To Launch
Know before you go
- 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
Photos
What travelers are saying
Outty’s summary of the themes that recur across 8 traveler reviews. Written by us, not quoted from reviewers.
Food and drink
4 mentionsThe tastings and food stops are a highlight for most reviewers.
Knowledge and storytelling
3 mentionsReviewers describe the commentary as informative rather than scripted.
The guide
2 mentionsTravelers single out the guide as the reason the experience works.
Traveler reviews
8 verified traveler reviews for Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour. Ratings and reviews provided by Viator and Tripadvisor.
Bourbon Country on a whole different Level
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.
Response from the operator: Hello Fellas. Sometimes the best times are the spontaneous ones. What a great day! Hope to see you same time next year. Angelique and the Sipping in the South enjoyed stepping in and sipping the day away!
via Tripadvisor
Truly Unparalleled Bourbon Tour/Guide
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.
Response from the operator: Thank you for the kind words. It was truly a pleasure spending the day with all of you. Your family is wonderful and I felt honored to be part of your experience. Families like yours remind me why I love what I do. I’m so glad you chose to share your time with me. Until next time Angelique and the team at Sipping in the south. Happy Thanks giving.
via Tripadvisor
Seal Team Six Precision - hospitality was next level
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.
via Tripadvisor
VIP BABY!
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
via Tripadvisor
Highly Recommend Angelique and Tuwanna
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.
via Tripadvisor
Good to know
- Duration
- 8 hours
- Free cancellation
- Non-refundable
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Wed, Thu, Fri, Sat, Sun
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 3
- Verdict
- Worth a Look
Why this scores 48
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Louisville.
How much does Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour cost?
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Prices start at $3200 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Louisville usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour take?
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Plan for about 8 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Louisville is not rushed.
Is Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour worth it?
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It holds an Outty Ranking of 48 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 8 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable food & drink in Louisville, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour?
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No. This experience is sold on a non-refundable basis, so only book a date you are confident about. Similar experiences in the city do offer free cancellation if flexibility matters more than price.
Is Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 8-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour?
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Around 3 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Louisville can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Louisville and add a light layer if any part of the 8-hour experience runs outdoors or after sunset.
Where does Private Kentucky Bourbon Trail - The Outlaws and Inlaws Tour start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Louisville within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Louisville?
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Louisville runs bourbon distillery tours and tastings along the Urban Bourbon Trail, Churchill Downs and Derby Museum visits, Louisville Slugger factory tours and river cruises. On Outty we rank every Louisville experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Historic Old Louisville Walking Tour, ORIGINAL Old Louisville Walking Tour seen in The New York Times!, Secrets of Louisville: 3hr NuLu Food & History Walking Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Louisville?
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April to June and September to November. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Louisville?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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