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Day Trips
Our day trips are designed as full thoughtfully paced experiences rather than a checklist of stops:
One-on-One Expert Planner
Private Transportation
Welcome Social
3-5 curated bourbon experiences that build on one another
Expert Guide
A southern inspired lunch
A balance of education and fun
Each day is shape around your group's vibe, whether that means a deeper dive into bourbon, or a more social experience, upgrade to a full weekend experience.

Most people hear “Bourbon Trail” and picture one straight path, like they're going to lace up their boots and hit the dirt road. It's actually not that at all. Bourbon in Kentucky is shaped by Five Bourbon Regions™ and each one has its own story, flavors, and rhythm. We have condensed it into three region for planning purposes and listed all the distilleries, not just those that are members of the Kentucky Bourbon Trail. Some of the best ones aren't even on that list.

Louisville Urban Bourbon brings city energy, vibrant nightlife, and an authentic speakeasy vibe, all set against the largest concentration of Old Victorian homes in the country.
Louisville/Urban (mostly tasting rooms)

Bardstown is the Bourbon Capital of the World, offering a blend of quaint charm and quiet evenings wrapped in Southern hospitality. It’s home to premier distilleries, boutique hotels, refined dining, and the kind of hospitality that makes every guest feel like family.
Bardstown/South Route:

Lexington is Bluegrass & Thoroughbred Country, shaped by rolling hills, white fences & world-famous horse farms. This region sits atop limestone aquifers, which gives the water a natural purity that helped define Kentucky bourbon. A place where bourbon and equestrian culture come together.
Lexington/Frankfort/East Route

Frankfort delivers historic roots, deep tradition, and true Kentucky craftsmanship. It’s where early delegates met and shaped the politics of Kentucky bourbon, giving this region its unmistakable legacy. Think barrel barns, live music, and good old-fashioned barn parties. Sip straight from the barrel and soak in the countryside charm. Bring your hats and boots; this is the authentic heart of Bourbon Country.

The Western Frontier is where bourbon’s backwoods history began. This region includes Owensboro, Paducah and Bowling Green, and is known for its ties to the early stills hidden deep in the countryside. It offers caves, lakes, national parks and wide open spaces that create a relaxed and adventurous side of Kentucky. It is the perfect region for guests who want bourbon paired with outdoor exploration, local character and weekends spent on the water.

Sip with the Owner right from Barrels and bottle one to go! This experience will be talked about for years to come.

Blending Bourbon is the hottest thing in the Market right now and now you can blend your own Bourbon too. The "J" in "J. Mattingly" refers to Jeff and often times you can find him around to sign your bottle.

Whiskey Thief is the best barn party you'll find in Bourbon Country. Its a great way to end the day on the trail less traveled -- drinking from barrels, live music, fire pits, cigars and corn hole. Doesn't get more country than that!

Great Rickhouse experience and the best cocktail class on the eastern trail. Great place to stop and get bar food. The staff behind the bar are fantastic!

Experience the perfect blend of artistry and craftsmanship at Kentucky's finest bourbon distillery. Bourbon tours, cocktails, and Lunch all on the 400 acres! Marg is a Bad Ass!

Want to Nerd out with the owners. Two guys buy the Old Crow Distillery and make an award-winning bourbon.

Good Bourbon and a Master Distiller for Over 70 years. Jimmy Russel is 90 years old and you'll want to be part of history before he's gone. Jim and Joretta Russel can be found signing bottles in the afternoons!

Makin' some good bourbon. The perfect mix of large enough but small enough. Peerless Toasted and Peerless Rum finish are some of my favorites.

This distillery has been brought back to life including stunning grounds. Enjoy the vibrant atmosphere enhanced with on-site food trucks and cocktails.

This distillery has been a sleeper, but recent upgrades to the visitors' center and restaurant makes it a must do! Also Heaven Hill's Bourbon has become some of the most sought after.

Another sleeper but the recent special releases has made it on my list. The tour and folks are great too. The tour includes not just about the distillery, but about the prohibition era. Great Stories.
Please reach us at tours@sippinginthesouth.com if you cannot find an answer to your question.
Bourbon has been a party of Kentucky since the late 1700’s. Louisville Kentucky is considered the ‘Wallstreet of Whiskey’ and Bardstown, Kentucky is the known as the ‘Bourbon Capital of the World’. On May 4, 1964, a congressional resolution passed naming bourbon as American’s
Native Spirit, giving it the same status as baseball and apple pie but more importantly other countries could no longer call their whiskey bourbon. Kentucky’s dominance in bourbon production, accounts for approximately 95% of the $9 Billion world’s supply, and is a testament to the ideal conditions and rich distilling heritage.
The state’s lush countryside not only provides a picturesque backdrop for the bourbon industry but the seasons and limestone filtered water also offers the essential natural resources that are critical for producing high quality bourbon.
With over 10 million barrels of bourbon aging in Kentucky, the state not only sustains its legacy as the heart of bourbon country but also continually enhances its reputation by producing bourbons of distinct and varied flavors This is where some of the most famous bourbon brands in the world are produced.
Numbers
10+ million barrels, each rickhouse holds 50,000 barrels, each barrel produces 200 bottles, each bottle $50. Bourbon is considered a currency and you can take that to the bank!
“Everyone knows the big names and they are good but there’s a whole world of bourbon experiences waiting just off the beaten path. Our curated tours don’t just take you to distilleries; they introduce you to hidden gems, exclusive pours, and stories you won’t hear anywhere else. Time and time again, our guests tell us, ‘We thought we knew bourbon, but this was something else entirely!’
Let us open the doors to places you didn’t even know you were looking for because the best experiences aren’t always the ones you can google. Come join us on the trail less traveled.
Yes, We do! Click Here
Absolutely! Sipping in the South loves to help, We've partnered with Louisville Guest Services and they have a great cheat sheet called LuvLuaVul. They also have one-on-one options if you need a more detailed itinerary and advance ticket purchases.
While we can accommodate larger groups of 30-50, we believe the magic of Bourbon Country lies in intimate, thoughtfully curated experiences. By keeping the groups smaller, we ensure you can fully immerse yourself in the trail less traveled - discovering hidden gems, engaging with distillers, and savoring the rich stories and history that make Kentucky Bourbon so special. This approach allows for deeper connections and a truly unforgettable journey. Groups of 8-12 per guide are ideal.
At Sipping in the South, a private bourbon tour means a fully personalized experience tailored to your chosen distilleries. It includes a private vehicle and expert guide for the day, ensuring concierge-level service from start to finish. Your guide curates the itinerary, selects the best experiences, shares insider knowledge, and highlights must-try bourbons.
We pair this service with high-end distillery experiences, selecting premium tastings and VIP options. While these activities may include other guests, choosing VIP experiences creates an exclusive atmosphere among bourbon enthusiasts.
If you’d like to have the Distillery experiences private as well, each ticket start at about $350 a person per Distillery. These selections have you sitting with owners and master distillers and trying Rare bourbons.
We recommend bringing an extra suitcase. You can check 5 Liters per person which equals 6.5 750ml bottles.
We recommend kicking off your Bourbon journey the night before with our 101 Welcome Social. This immersive session teaches you the art of properly nosing and sipping bourbon. We also recommend including a bourbon mixology class. By the end of the day with us, we guarantee you'll have unleashed your inner Bourbon enthusiast -- or, as we like to say, created a true Bourbon Monster.
In Bourbon Country allocated refers to a limited amount. Distilleries only release a certain number of bottles each day making them highly sought after and difficult to find. These exclusive releases add to the excitement and allure of the Bourbon Experience. Our Expert Sipping Directors closely monitor distilleries and their special releases ensuring your day includes the most exclusive and memorable Bourbon experiences possible
Absolutely! At Sipping in the South, we scout liquor stores in advance to ensure your Bourbon tour is as memorable as possible. We've identified hidden gems or "honey holes" known for carrying rare and allocated bottles. During your tour, we include 30 minutes to stop at a couple of these trusted locations, giving you the chance to uncover something truly special. Suppose you're looking for an even deeper dive into rare bottle hunting. In that case, we offer an exclusive experience called Hunting with Angelique - a tailored journey dedicated to uncovering the most elusive Bourbon Treasures.
Absolutely! Sipping in the South loves to help create the perfect Bourbon tour experience. To tailor the tour to your needs, we'll just need a bit more information. What's the date you're looking at? How large is your group? What's the makeup of your group? (friends, family, coworkers, couples) Where will your group be staying? Do you want to incorporate golf, horse racing, or sitting with a master bourbon connoisseur? Does he have a favorite bourbon or a must-do distillery? Just fill out the form above and we will take it from there!
We understand that life happens, so we’ve kept our policy simple:
✨ If something happens that’s beyond anyone’s control like distillery closures or travel interruptions we’ll provide a voucher to rebook.
To cancel, send us an email at tours@sippinginthesouth.com or text us at 502-755-5105.
Every tour comes with transportation, three distilleries, lunch and guides.You pick the region to visit, the style of vehicle and the level of expertise behind the wheel. Private and custom adventures from $295 to $450 (four guest minimum).
The Kentucky Bourbon Trail is often thought of as a linear path you follow, but it is really a paid marketing program for distilleries and transportation companies. Because of that, it does not include all 5 Bourbon Regions. Many of the most authentic and historic distilleries are not even included. By not being tied to the program, we give our guests more. We can take you to both the famous names and the hidden gems, creating an experience that feels more flexible, more exclusive, and more authentic and much less scripted.
Louisville, Kentucky 40203, United States
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