The Kentucky Bourbon Trail offers an unparalleled immersion into America’s native spirit, winding through rolling bluegrass countryside, historic distilleries, and charming small towns. While you could plan this journey yourself, a specialized travel advisor transforms your trip from a series of distillery visits into a curated, seamless experience.

As your dedicated food and beverage travel advisor with a background as a former sommelier and pastry chef, I bring specialized knowledge to planning your bourbon journey. My expertise in spirits allows me to secure exclusive distillery experiences, arrange private tastings with master distillers, and access limited-edition releases. You’ll enjoy an exceptional Kentucky bourbon adventure—all without the stress of complex planning.

Day 1: Louisville – The Gateway to Bourbon Country

Arrival & Settling In

Your bourbon adventure begins in Louisville, the official starting point of the Kentucky Bourbon Trail. Upon arrival, check in to the historic Hotel Distil, perfectly situated in the heart of Louisville’s famed Whiskey Row. This boutique hotel beautifully blends historic architecture with modern luxury, making it the ideal base for the first leg of your journey. Maybe we arrange for you to enjoy the hotel’s exclusive In-Room Bourbon Cart Experience, but be sure to join the hotel’s signature 7:33 Nightly Repeal Day Toast in the lobby.

Afternoon: Free Time to Explore Whiskey Row

After settling in, take some time to explore Louisville’s historic Whiskey Row. This stretch of Main Street once housed the bourbon industry’s shipping and trading offices and has been beautifully revitalized with restaurants, bars, and distilleries. For those looking to track their visits with the official Bourbon Trail Passport, now’s a great opportunity to pick one up at the Bourbon Trail Welcome Center.

Late Afternoon: Angel’s Envy Distillery Experience

Your first official distillery experience begins at Angel’s Envy, just a short walk from your hotel. This modern distillery is known for finishing its bourbon in port wine casks (amongst other finishes), creating a uniquely smooth and nuanced spirit.

Dinner Recommendation: After your tasting, enjoy dinner at Decade, a stylish restaurant known for its seasonal cuisine and impressive bourbon selection. Located near your hotel, Decade offers a perfect introduction to Louisville’s celebrated food scene with dishes that complement your bourbon journey.

Day 2: Exploring Louisville’s Bourbon Heritage

Morning: Free Time to Explore

Start your day with breakfast at Butchertown Grocery Bakery, known for its outstanding pastries, artisan breads, and excellent coffee. Then, take the morning to explore more of Louisville at your leisure or maybe rest and recover. Consider visiting the Louisville Slugger Museum, Muhammad Ali Center, or simply strolling through the charming downtown area.

Afternoon: Michter’s Discovery Tour and Tasting

In the afternoon, head to Michter’s Fort Nelson Distillery on West Main Street. This historic building houses a functional distilling system from the 1800s alongside modern production facilities.

Evening Recommendation: Experience Louisville’s urban bourbon scene with pre-dinner drinks at North of Bourbon, a hip spot showcasing rare bourbon selections and Southern-meets-Cajun influences. Follow with dinner at the legendary Jack Fry’s, a Louisville institution since 1933 known for its classic ambiance and refined Southern cuisine.

Day 3: From Louisville to Bardstown – The Bourbon Capital of the World

Morning: Maker’s Mark Distillery Tour and Tasting

Check out of your Louisville hotel, where your private driver will be waiting to transport you on the next leg of your journey. Your first stop is Loretto, Kentucky, home to the iconic Maker’s Mark Distillery. With its distinctive red wax-dipped bottles and picturesque grounds, Maker’s Mark offers one of the most visually stunning distillery experiences, so be sure to get there with plenty of time to explore.

Afternoon: Travel to Bardstown and Heaven Hill Experience

After your Maker’s Mark experience, your driver will take you to Bardstown, known as the “Bourbon Capital of the World.” Check in to the charming Bardstown Motor Lodge, a boutique property offering modern amenities with vintage flair in the heart of this historic town.

In the afternoon, your driver will escort you to the Heaven Hill Bourbon Experience for their exclusive Bottled-in-Bond Warehouse Tour and Tasting. If time allows, we’ll arrange for you to stop by the Bar at Willett for drinks before heading back to Bardstown.

Evening in Bardstown

Spend the evening exploring Bardstown’s charming downtown with its historic buildings and boutique shops. Enjoy dinner at Toogie’s Table, the chef-led farm-to-table restaurant conveniently located at the Bardstown Motor Lodge, showcasing local Kentucky ingredients and bourbon-infused cuisine. After dinner, enjoy a bourbon and s’mores kit by the property’s fire pits—a perfect way to unwind while savoring one last pour from the day’s discoveries.

Day 4: Bardstown to Lexington – Following the Bourbon Trail East

Morning: Bulleit Frontier Whiskey Distillery

After breakfast, your driver will pick you up from the Bardstown Motor Lodge to continue your bourbon journey. Your first stop is Shelbyville to visit Bulleit Frontier Whiskey Distillery. Known for their high-rye bourbon recipe, Bulleit offers a modern distillery experience in a stunning contemporary facility.

Late Morning: Woodford Reserve Distillery

Your journey continues with a scenic drive through Kentucky’s famous horse country to reach Woodford Reserve Distillery in Versailles. This National Historic Landmark is set among rolling hills and offers one of the most picturesque settings on the Bourbon Trail.

Afternoon: Check in to The Manchester in Lexington

After your Woodford Reserve experience, your driver will take you to Lexington, the heart of Bluegrass Country, where you’ll check in to The Manchester, a sophisticated boutique hotel built on the site of Central Kentucky’s first registered bourbon distillery from 1865. Don’t miss the opportunity to visit their stylish rooftop bar, The Lost Palm, offering craft cocktails with stunning views of downtown Lexington.

Late Afternoon: Buffalo Trace Hard Hat Tour

After a brief rest at your hotel, take a short rideshare to Frankfort for the Buffalo Trace Distillery Hard Hat Tour, a unique behind-the-scenes look at America’s oldest continuously operating distillery and a National Historic Landmark.

Evening in Lexington

Return to Lexington for the evening. Enjoy dinner at Dudley’s on Short, a Lexington institution housed in a historic bank building in the heart of downtown. The restaurant is known for its seasonal menu featuring local ingredients andan impressive bourbon selection.

Day 5: Final Day – Completing Your Bourbon Trail Journey

Morning: Four Roses Distillery – A Taste of History

Take a rideshare to begin your final day with a visit to Four Roses Distillery in Lawrenceburg. With its unique Spanish Mission-style architecture, Four Roses stands out as one of the most distinctive distilleries on the trail.

Early Afternoon: Wild Turkey Distilling Co. Production Tour

Complete your Bourbon Trail journey at the Wild Turkey Distillery in Lawrenceburg. Perched on a scenic cliff overlooking the Kentucky River, Wild Turkey offers breathtaking views alongside their excellent bourbon.

Departure

After your Wild Turkey experience, head home with your newfound bourbon expertise (and hopefully a few prized bottles in your luggage)—ready to host the most impressive bourbon tastings in your neighborhood!

Distillery Reservations: Timing is Everything

Securing the right reservations at the right times is critical for a successful Kentucky Bourbon Trail experience. Here’s what you need to know (if trying to book these distilleries on your own):

Louisville Distilleries

• Angel’s Envy: Reservations open 90 days in advance and fill quickly, especially for their Finishing Room and Bottle Your Own experiences.
  
• Michter’s Fort Nelson: Tours book out 60-90 days in advance. For bourbon enthusiasts seeking a truly exceptional experience, the exclusive Legacy Tour is only offered once per month by a senior member of the Michter’s team.

Bardstown Area Distilleries

• Maker’s Mark: Be sure to arrive at Maker’s Mark early to allow time to explore their extensive grounds and your tasting. Note that tour tickets are not sold onsite and must be purchased in advance online.
  
• Heaven Hill: Their Bottled-in-Bond experience requires advance booking up to 3 months out.

Lexington Area Distilleries

• Bulleit: Less crowded than others, but still requires booking 30-45 days out. The morning tour time provides a perfect start before continuing to Woodford Reserve.
  
• Woodford Reserve: One of the most popular destinations requiring 3-4 months advance booking, especially during Derby season (April-May) and for super limited offerings like the VIP Master Distiller Experience.
  
• Buffalo Trace: Their Hard Hat Tour is one of the most coveted experiences on the trail (as are all their tours). Buffalo Trace releases booking slots every Wednesday at 10:00 am, exactly two months before tour dates. Tickets will be gone within minutes of release, which is why you need an expert travel planner to secure these highly sought-after experiences.
  
• Four Roses: Generally easier to book with 30-60 days’ notice.
  
• Wild Turkey: Can typically be booked with 30 days’ notice.

Working with an expert travel advisor means all these complex reservations will be handled seamlessly, with optimal timing that minimizes travel time while allowing you to enjoy each distillery experience fully.

Sample Add-On Experiences

Enhance your Bourbon Trail journey with these optional add-on experiences that I can arrange:

• Bourbon Blending Workshop: Create your own unique bourbon blend under expert guidance.
• Cooperage Tour: Visit a barrel-making facility to understand how the charred oak influences bourbon’s flavor.
• Bourbon Historian Private Tour: Travel with an expert bourbon historian who provides deep insights at each stop.
• Cocktail Masterclass: Learn to craft classic and innovative bourbon cocktails from award-winning mixologists.
• Private Barrel Selection: Work alongside a master distiller to select a private barrel for purchase (if you need A LOT of bottles of whiskey at home).
• Food & Bourbon Pairing Masterclass: Learn the art of pairing bourbon with artisanal chocolates, cheeses, and southern cuisine.

Planning Your Bourbon Trail Adventure with an Expert Travel Planner

Beyond the distillery tours and tastings, the Kentucky Bourbon Trail delivers immersive encounters with master distillers, behind-the-scenes access to production floors, and the rare opportunity to sample straight from the barrel—experiences impossible to arrange without insider connections. By working with me to plan this experience, your travels will be transformed from simple distillery tastings into immersive bourbon experiences crafted specifically for your preferences and interests.

Whether you’re a bourbon aficionado or just beginning your whiskey journey, a well-planned Bourbon Trail experience creates memories that will last long after the last sip.

Click the “Start Planning Now” button below to begin planning your personalized Kentucky Bourbon Trail experience, and let me craft a journey as unique as the bourbon you’ll discover.