Bourbon Itineraries
Plan a unique trip to Bourbon Country with one of our suggested itineraries!
While it is possible to see every distillery if you spend a week in Bourbon Country, getting to every wonderful bourbon experience that can be had, from a chocolate shop with THE best bourbon balls to every stop on the Urban Bourbon Trail, is a little ambitious. We’ve designed some itineraries to help you narrow down what appeals to you most. They are created by region, budget and interest from the locals who know their area best. You may want to mix it up like a cocktail and make your plan using these suggestions. Then, send us what you did, and we may post your schedule as a plan for other bourbon lovers to follow.
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ONE DAY URBAN BOURBON EXPERIENCE™
Louisville: Kentucky’s largest city is home to nearly a dozen bourbon distilleries and the cocktail experience of the Urban Bourbon Trail. Whet your appetite with this one-day tour plan.
Breakfast:
PLEASE & THANK YOU – Start your day with a locally baked pastry in the NULU district. This hip coffee/music shop combo is known for its chocolate chip cookies and wide selection of vinyl records… and is a favorite place of Teddy Abrams—the young, hip Music Director/Conductor of the Louisville Orchestra.
COPPER & KINGS AMERICAN BRANDY – Based in Butchertown, Copper & Kings makes dynamic American-style brandy. Tour this modern distillery, where guests will learn about the brandy distilling process. Visitors will also tour the 75% underground, naturally climate-controlled brandy cellar where the barrels are sonically aged through music.
ANGEL’S ENVY DISTILLERY – Opened in 2016 along historic Whiskey Row, Angel’s Envy offers visitors a fully operational urban distillery experience. See the distillation process from beginning to end, with the tour ending in the Finishing Room with a tasting of Angel’s Envy.
Lunch:
DOC CROW’S SOUTHERN SMOKEHOUSE & RAW BAR – An official Urban Bourbon Trail stop, Doc Crow’s is nestled in Downtown Louisville’s heart of Whiskey Row. It currently sits where the well-known Bonnie Bro. The distillers’ warehouse previously thrived. Doc Crow pays homage to the father of bourbon, Dr. James C. Crow, who paved the way for Kentucky bourbon to be born. So stop by for a glass of bourbon and various southern treats.
EVAN WILLIAMS BOURBON EXPERIENCE – Located on Louisville’s Museum Row, it features an artisanal distillery, tours, tastings and more. Celebrating the legacy of Evan Williams, Kentucky’s first distiller, this immersive experience brings to life the history and tradition of Kentucky’s native spirit.
FRAZIER HISTORY MUSEUM – Along Museum Row, the Frazier is the Kentucky Bourbon Trail® Welcome Center and the Official Starting Point of the Kentucky Bourbon Trail®. Various Bourbon tasting experiences are offered, including a craft-your-own cocktail experience and private tours and tastings. They also have three exhibits that highlight bourbon’s history in Kentucky: The Spirit of Kentucky exhibition gives an in-depth look at Bourbon whiskey and is the perfect spot to learn about America’s native spirit; Pappy Van Winkle: The Van Winkle Family Collection exhibition features items from the Van Winkle family archives, including original photographs, bottles, and unique Bourbon-related items from the archives; the Bourbon Bottle Hall showcases a massive collection of over 250 varieties, this gallery contains every bottle of Bourbon currently in production in the state of Kentucky.
KENTUCKY PEERLESS DISTILLERY – While it is one of the newest distilleries in downtown Louisville and home to the only urban bourbon rickhouse in the city, Kentucky Peerless is an old family brand that is steeped in four generations of rich history dating back to the 1860s.
BARDSTOWN BOURBON CO. DOWNTOWN TASTING ROOM – While this isn’t a distillery tour, you can do that at the Bardstown, KY location. This is a newer tasting room in downtown Louisville that offers a state-of-the-art, modern bourbon experience. This location features interactive education and tasting experiences, innovative craft cocktails, augmented reality, and of course, curated retail merchandise and exclusive bottles.
Happy Hour:
THE GARDEN & GUN CLUB– Intimate and inviting, the Garden & Gun Club at Stitzel-Weller Distillery writes a new chapter in Southern hospitality. The premier cocktail bar and lounge brings the defining Southern lifestyle brand to life with a curated menu of elevated cocktails and a modern take on some of our favorite classic Southern dishes.
Dinner:
THE LOBBY BAR AT THE BROWN HOTEL – Contemporary classic meets old-world opulence at The Brown Hotel’s spectacularly beautiful and surprisingly unstuffy Lobby Bar. A popular spot for the next generation of Louisville merrymakers, this glamorous, gilded space balances its history with modern touches and sophisticated tastes. Indulge in classic comfort food and kick back with a hand-crafted cocktail. The Hot Brown, Louisville’s most famous dish and creation of the Brown Hotel, and a slice of Derby Pie pair perfectly with their hand-selected bourbon flight.
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HIGH STAKES ROOFTOP GRILL – Nestled in the heart of downtown Louisville. Indulge in classic American dishes made with the freshest locally sourced ingredients while enjoying spectacular rooftop views. Explore their three unique spaces: a lively inside-out racetrack bar, a serene rooftop lounge, and an intimate dining room. While you’re in town discovering the best Bourbon’s in the world, make a stop at this incredible restaurant while taking in breathtaking views and eating delicious food.
Nightlife:
LIVE MUSIC & SPEAKEASIES – Stay downtown to experience live music at Stevie Ray’s Blues Bar or Merle’s Whiskey Kitchen. Or, opt for a game of bowling in the Omni’s speakeasy bar, Pin + Proof. Looking for an elevated cocktail experience? Check out Seven. If it’s speakeasies you’re looking for, head to the alley behind Whiskey Row to Hell or High Water, or find your way behind the mini-market at Hotel Genevieve to the Lucky Penny.
*Restaurants listed are recommended based on location with the itinerary stops before and after meals and in relation to the theme of the itinerary. For more dining ideas, search by cuisine or neighborhood.
THE BOURBON CAPITAL
Bardstown: Known as the “Bourbon Capital of the World”, historic Bardstown has long been a cradle for America’s native spirit
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Bardstown Area in a Day
Note: this suggested itinerary assumes Louisville as your starting point, taking you first through Shepherdsville for the Jim Beam tour, 25 minutes from downtown Louisville. Then Bardstown will be another 20 minutes from Shepherdsville.
8:15 a.m. – Depart Louisville for Shepherdsville, KY
8:45 a.m. – Arrive at Jim Beam for 9 am tour
10:25 a.m. – Depart Jim Beam for Bardstown, KY
10:45 a.m. – Arrive at Heaven Hill Distillery
12:15 p.m. – Lunch at one of Bardstown’s signature spots: Mammy’s Kitchen or The Old Talbott Tavern
Old Talbott Tavern – the oldest western stagecoach stop in America with many bourbon barons as former owners since the late 1700s.
Mammy’s Kitchen – is known for bourbon burgers, country cooking, and mile-high meringue pies.
1:30 p.m. – Depart for Maker’s Mark in Loretto, KY
2:00 p.m. – Tour Maker’s Mark; depart at 3:15 to return to Bardstown
OPTION: You could save the 1-hour round trip to Maker’s and have more time downtown to tour Willett Distillery (a more prominent craft distiller) or Barton’s 1792 (a more vintage industrial-type tour than the others). Both are in Bardstown, and the tours are roughly 1 hour each.
3:45 p.m. – Shopping Downtown Bardstown (the shops will close between 5 and 6)
Rand McNally named Bardstown the Most Beautiful Small Town in America. One reason for this is its picture-perfect downtown streets teeming with boutiques and eateries.
5 p.m. – So many options here. Cocktails, a Dinner Train, Overnight or back to Louisville.
My Old Kentucky Dinner Train – Dine in a vintage railroad car serving up American meals during a scenic rail journey in the Kentucky countryside, lasting several hours.
Happy Hour or Dinner in Bardstown – If you didn’t have lunch at the Old Talbott Tavern, this is an excellent spot for a cocktail. Other drink and dinner options are the new American fare, served in the Colonial tavern of the Harrison-Smith House or Rickhouse. Steaks and a large bourbon list feature at the underground, brick-walled eatery in the basement of a historic school.
Stay the night: Tuck into one of Bardstown’s charming B and B’s, like the Bourbon Manor, and spend an extra day in the Bourbon Capital. Six distilleries are located in or near Bardstown: Barton 1792, Willett Distillery, Heaven Hill, Maker’s Mark, Jim Beam, and Four Roses/Cox Creek.
The EXTRAS……
Best Snapshot Spot:
Lock and load for a selfie at the prison stocks in the Old County Jail (now Jailer’s Inn B&B).
Soak Up Culture:
Tour one of the world’s most recognizable homes – Federal Hill, also known as My Old Kentucky Home – immortalized by composer Stephen Foster, and watch the Broadway-style musical, “The Stephen Foster Story.”
THE KENTUCKY CAPITAL
Frankfort: Kentucky’s state capital, Frankfort, is filled with Bourbon tradition, and the oldest continuously operating distillery in the US calls this city home.
.Visit The Capital City
Nestled along the banks of the Kentucky River, Frankfort is perfectly positioned between Louisville and Lexington. The city’s rich tapestry of culture and natural beauty captivates visitors and locals alike. Steeped in a legacy that spans centuries, the city boasts architectural marvels like the majestic Kentucky State Capitol and the historic Old Governor’s Mansion. At the same time, its picturesque downtown area invites exploration with quaint shops, vibrant eateries, and lively community events. Surrounded by rolling hills and verdant landscapes, Frankfort seamlessly blends the old with the new, which extends to its role in the bourbon industry with nearby distilleries crafting some of the finest spirits in the world, adding another layer of flavor to the city’s already rich tapestry. Discover all there is to do over two nights and two days in the capital city.
Day One
Begin your day with breakfast at a local favorite known for its delicious Southern comfort food and featured on the Food Network’s “Diners, Drive-ins, and Dives,” Cliffside Diner. Or check out B’s Bakery, situated along Main Street in the heart of downtown, for your fill of made-from-scratch donuts, pastries, muffins, and so much more.
After breakfast, step back in time to a distillery inspired by European architecture. In 1887, Colonel E.H. Taylor built the Old Taylor Distillery, which became the birthplace of Bourbon Tourism. In 2014, the ruins of the grand distillery were brought back to life and given a second life as Castle & Key Distillery.
From there, journey over to Glenns Creek Distillery, where the owners offer hand-crafted, single barrel and barrel strength bourbon, including a special bourbon created from the original fermentation tanks from Old Crow Distillery.
Lunch and Dinner Suggestions:
- The Stave, a Kentucky Bourbon Trail restaurant and bourbon bar nestled on the banks of Glenn’s Creek halfway between Woodford Reserve and Castle & Key Distilleries, features a Kentucky-inspired menu.
- Bourbon on Main, a restaurant and bar specializing in Southern cuisine and an extensive selection of bourbons.
- Serafini, across from the old State Capitol building, sits Serafini, where the menu selections focus on local ingredients that are combined to showcase the best of Italy with traditional southern food.
Day Two
For a grab-and-go breakfast before heading out on day two of bourbon experiences, OMG Donuts is a “sweet” way to start the day. You can also stop by either Kentucky Coffeetree Café on Broadway Street or Pop’s Diner across from Buffalo Trace Distillery.
Now that you are properly fueled, it is time to tour the most award-winning distillery in the world, Buffalo Trace Distillery. Name for the ancient buffalo that roamed the area, Buffalo Trace, a National Historic Landmark, one of the oldest continuously operating distilleries in America, and is home to well-known bourbons like Eagle Rare, E.H. Taylor, Jr., W.L. Weller, and Pappy Van Winkle. With various tours to choose from, all the tour experiences are complimentary, but reservations are highly recommended. For a unique tour experience during warmer months, join Canoe Kentucky’s Bourbon Paddle Tour, where guests paddle down the Kentucky River to the distillery for a tour, tasting, and lunch.
From there, it’s a short trip to J. Mattingly Distillery, where the sixth generation has perfected the first-of-its-kind custom bourbon blending process. Guests take on the role of distiller as they blend their own bottle from proprietary barrels and choose their own bottle, label design, wax color to seal the bottle, and name their bourbon blend.
Lunch and Dinner Suggestions Nearby:
- Limewater Bistro + Bar is a fine dining restaurant in the historic 1815 Glen Willis house that sits on the Kentucky River.
- Sage Garden Café, combining homegrown with homemade, Sage Garden Café showcases regional favorites.
- West Sixth Brewery Farm is a unique 120-acre farm experience that combines a taproom, trails, and food trucks.
Wind down each night at one of these Bourbon Bars:
- HOC: A Bourbon Library, the House of Commons Bourbon Library is a curated, one-of-a-kind experience for everyone from Bourbon novices to Bourbon aficionados.
- The Cooperage Bar, originally a Wild West-style saloon, the Cooperage Bar was resurrected in 2019 into an upscale bourbon bar in the heart of Frankfort that maintains some of the charm of its past.
- The Howser Tavern, a flavorful experience is ensured at the Howser Tavern with twists on classic recipes to experimental mixology.
- Capital Cellars, taste fine Kentucky Bourbon in the heart of the bourbon trail where an unparalleled selection of bourbon awaits.
Looking for more bourbon experiences in the area to add to your “must-do” list? Check out:
- Woodford Reserve Distillery
- Whiskey Thief Distilling Co.
- Colonel E.H. Taylor Audio Tour
- Rebecca Ruth’s Candy Tours and Museum to stock up on bourbon balls and chocolates before heading home.
First-Timer’s Two-Day Bourbon Adventure
Dive into Kentucky’s bourbon heritage with this two-day first-timers itinerary, exploring top distilleries and savoring the finest flavors in Louisville and Bardstown.
Day 1: Louisville
Morning:
EVAN WILLIAMS BOURBON EXPERIENCE: Start your day with a tour and tasting at one of the oldest distilleries in Kentucky. Learn about the history of bourbon and enjoy a guided tasting.
Lunch:
JACK FRY’S: Enjoy a meal at this historic restaurant known for its high-end Southern fare and old-world charm. It’s a perfect spot to relax and eat some delicious food paired with bourbon.
Afternoon:
ANGEL’S ENVY DISTILLERY: Visit this modern distillery for a tour and tasting. Learn about their unique finishing process in port wine barrels.
Evening:
BOURBONS BISTRO: Savor dinner at this renowned restaurant, which offers an extensive bourbon menu. Try a bourbon flight to sample different varieties.
Day 2: Bardstown
Morning:
MAKER’S MARK DISTILLERY: Start your trek to Loretto for a tour of this iconic distillery. Explore the beautiful grounds and sample their handcrafted bourbon.
Lunch:
THE RICKHOUSE RESTAURANT & LOUNGE: Enjoy a hearty lunch in Bardstown, known as the Bourbon Capital of the World.
Afternoon:
HEAVEN HILL DISTILLERY: Visit this historic distillery for a tour and tasting and learn about its extensive bourbon portfolio.
Evening:
OLD TALBOT TAVERN: Dine at one of the oldest western stagecoach stops in America. Enjoy a meal paired with local bourbons.
Optional Evening Activity:
BOURBON TASTING AT BARDSTOWN BOURBON COMPANY: End your day with a tasting at this innovative distillery. Explore their modern facilities and sample unique bourbons.
This itinerary offers a mix of historic and modern distilleries, delicious food, and plenty of opportunities to taste Kentucky’s finest bourbons. Enjoy your bourbon adventure!