In Kentucky, history and heritage are cause for celebration.
That’s what six tour-operator readers of The Group Travel Leader discovered during a four-day familiarization tour in May to some of the Bluegrass State’s most popular attractions. Hosted by the Kentucky Department of Tourism, this Great Gatsby-themed tour showcased historic sites throughout the state that inspired the famous novel, as well as other places related to Kentucky’s bourbon industry, horse-racing heritage and more.
During the trip, participants got to know the Northern Kentucky region on the Ohio River then traveled to Lexington, which is at the center of the state’s beautiful horse farm country. In Louisville, they enjoyed opulent historic accommodations, sampled from some of the city’s many bourbon distilleries and enjoyed an iconic evening at the races.
Follow along on this itinerary to start planning a Kentucky tour for your groups.
Day 1
• Arrival in Newport
• Revival Vintage Bottle Shop & Bar
• Newport Gangster Tour
• Dinner cruise with BB Riverboats
• Wiseguy Lounge
Tour planners from around the country traveled by plane and car to the Northern Kentucky region, an area on the banks of the Ohio River that includes cities such as Newport and Covington. After checking in at their hotel for the night, Aloft Newport on the Levee, they started the tour by visiting Revival Vintage Bottle Shop & Bar in Covington, where they got to learn about and sample some rare and historic bourbon and other whiskeys from around the state. Afterward, they took a walking tour of Newport with a guide from American Legacy Tours, who told them the secrets of Newport’s life as a gangster hot spot during the Prohibition era. Next was a delicious dinner and scenic cruise with BB Riverboats, followed by a nightcap at Wiseguys Lounge in Covington.
Revival Vintage Bottle Shop & Bar
Throughout Kentucky’s illustrious bourbon distilling history, hundreds of distilleries have produced thousands of rare, collectible whiskeys. At Revival Vintage Bottle Shop & Bar, a bar, tasting room and vintage shop in Newport, visitors can taste samples from 150–200 rare bourbons, including some distilled as long ago as 1914. The establishment offers samples as small as a quarter ounce so enthusiasts can taste normally expensive bourbons at reasonable prices. The FAM group enjoyed a signature cocktail, a bourbon tasting and a tour of the vintage bottle display area.
Newport Gangster Tour
Guides from American Legacy Tours describe the city of Newport as “Vegas before Vegas” and tell stories of the area’s rowdy Prohibition past during their Newport Gangster Tour. Guests learn about the bootlegging industry that thrived in Newport during Prohibition, as well as the more than 30 casinos that once operated in town, many under the direction of mob bosses. The tour features a stop at the home of the man who invented the Tommy gun, as well as other sites related to the area’s colorful past.
BB Riverboats
One of the most beloved activities along the Cincinnati and Northern Kentucky waterfronts, BB Riverboats offers an array of cruising options up and down the Ohio River. Groups can sail on one of two paddle wheeler-style vessels, the Belle of Cincinnati or the River Queen, both of which offer excursions with beautiful scenery, delicious food and options for live music. During their cruise, the FAM group enjoyed special Roaring ’20s-inspired dishes and got to visit the ship’s captain in the pilot house.
Day 2
• Depart for Lexington
• Lunch and tour at Mill Ridge Farm
• Kentucky Horse Park
• Bluegrass Distillers
• Dinner at J. Render’s Southern Table & Bar
The group began the next day with breakfast at the hotel in Covington then started the journey about 75 miles south to Lexington. When they arrived, they headed to Mill Ridge Farm to learn about the area’s legacy of Thoroughbred farming, meet horses up close and enjoy a delicious lunch. Next up was a visit to Kentucky Horse Park, the city’s signature attraction offering a museum, horse shows and more. From there, they made the short trip to the town of Midway to enjoy a tour and bourbon tasting at Bluegrass Distillers. They returned to Lexington to check into The Campbell House, a Curio Collection by Hilton property, then enjoyed an evening of smoked meat and Roaring ’20s decor at J. Render’s Southern Table & Bar.
Mill Ridge Farm
Though Mill Ridge Farm was founded in 1962, Kentuckians have been raising Thoroughbreds on its land since the 1800s. Today, the farm is known for breeding and caring for some of the world’s top racehorses. On a tour, guests can learn about the farm’s history, drive through the scenic property, visit the breeding barn and even spend time petting and feeding some of the horses that live there. The travel planners had a charming catered lunch in a barn on the property, an experience that is also available to tour groups.
Kentucky Horse Park
Founded by the state of Kentucky to educate visitors about all things equestrian, Kentucky Horse Park features two museums, competition grounds, live shows and dozens of horses. At the International Museum of the Horse, visitors learn about the history of horse farming and can see a collection of many Kentucky Derby and Triple Crown trophies. A horse-drawn trolley tour is a great way to explore the entire complex. At the Hall of Champions, visitors can meet horses that have retired after illustrious racing careers, and equine-showcase experiences introduce visitors to many breeds of horses from around the world.
Bluegrass Distillers
In Midway, a village about 15 minutes away from Lexington, Bluegrass Distillers is a family-owned distillery that makes small-batch bourbons, including its signature blue corn whiskey. Guests can tour the distillery, which is located on a historic farm, to see how the products are fermented, distilled and bottled. The FAM group also enjoyed a welcome cocktail and a guided tasting experience in the converted 1835 farmhouse. A ranger led the tour group around the site — now a national monument — to point out its French-inspired architecture, tell them about the enslaved people who built its walls and show them its authentic Civil War cannons.
Day 3
• Depart for Louisville
• Seelbach Roaring ’20s Tour
• Lunch at Doc Crow’s Southern Smokehouse & Raw Bar
• Frazier History Museum
• Louisville Slugger Museum & Factory
• Tour and dinner at Paristown Pointe
On the third day of the tour, the group departed Lexington early and headed about 75 miles west to Louisville, the largest city in the state. Upon arriving, they checked into the Seelbach Hilton, which would be home for the next two nights, and enjoyed a tour of the 1905 property, including spaces where F. Scott Fitzgerald drew inspiration for “The Great Gatsby.” Next, they ate lunch downtown at Doc Crow’s Southern Smokehouse & Raw Bar then visited the Frazier History Museum for an up-close experience with 1920s artifacts and a bourbon tasting. From there they took a short walk across the street to the Louisville Slugger Museum & Factory, where they learned about the history and manufacturing process of the most famous piece of equipment in sports history. After a short break at the hotel, they went to the Paristown Pointe neighborhood for dinner, where they got a preview of Uncle Boojie’s, a soon-to-open distillery and event venue, as well as a speakeasy soiree dinner.
Frazier History Museum
Located on Main Street, also known as Louisville’s Museum Row, the Frazier History Museum tells stories from Kentucky history using artifacts and live interpretations. Among the highlights is an exhibition called America’s Native Spirit that features details of Kentucky’s bourbon heritage, as well as a collection of more than 400 bottles from distilleries around the state. A secret door in the bottle room leads to a speakeasy, where the FAM group had a private experience with Prohibition artifacts from the collection, including flapper dresses and a prescription for medicinal whiskey. The experience ended with a tasting of three Kentucky bourbons.
Louisville Slugger Museum & Factory
Also on Museum Row, a 120-foot-tall sculpture of a baseball bat leaning against a brick building marks the site of the Louisville Slugger Museum & Factory. Visitors can tour the factory to see how the legendary bats are made to the individual specifications of Major League players. The accompanying museum details the history of the company and some of the players who have used its bats. In an interactive exhibit called Hold a Piece of History, visitors can take photos holding Louisville Slugger bats used in actual games by luminaries such as Derek Jeter, Cal Ripken Jr., Willie Mays and Babe Ruth.
Paristown Pointe
In Paristown, a seven-acre arts district in central Louisville that has been recently rejuvenated by local developers, groups will find a variety of inviting experiences. Chief among them is a tour of Stoneware & Co., which has been making fine ceramic dishes and other items by hand in Louisville since 1815. The development also has The Village Market Food Hall & Bar, The Café Southern Kitchen and Uncle Boojie’s, a new distillery crafting bourbon from a 200-year-old family recipe. The FAM group got a preview of the soon-to-open tasting room at Uncle Boojie’s and a delightful Roaring ’20s speakeasy dinner in a private space at the Stoneware & Co. showroom.
Day 4
• Breakfast and tour at The Brown Hotel
• Evan Williams Bourbon Experience
• Trolley de ‘Ville
• Lunch at Bristol Bar & Grille
• Kentucky Derby Museum
• Twilight Racing at Churchill Downs
The group began their second day in Louisville with a tour and breakfast at The Brown Hotel, birthplace of Kentucky’s famous Hot Brown open-face sandwich. Next, they had an immersive historic bourbon tasting at the Evan Williams Bourbon Experience, followed by a wonderful overview tour of the city with Trolley de ‘Ville. After lunch at the Bristol Bar & Grille Downtown, they headed to Churchill Downs, where they took in a film, exhibits and hands-on experience at the Kentucky Derby Museum before heading up to the grandstands for an evening of food, drinks and Thoroughbred racing at twilight.
Evan Williams Bourbon Experience
Also located on Museum Row, the Evan Williams Bourbon Experience introduces visitors to one of Kentucky’s most historic bourbon brands. Tours cover 200 years of distilling on the Louisville waterfront with immersive films and an inside look at a micro-distilling operation inside the museum. The facility also features a basement speakeasy, where the FAM group enjoyed a tasting experience led by a costumed interpreter who shared details about Louisville’s Great Gatsby history in addition to samples of five signature whiskeys.
Trolley de ‘Ville
Operating city tours on open-air vehicles, Trolley de ‘Ville is an excellent way to showcase the diversity of Louisville’s downtown and surrounding neighborhoods. The tour starts near the Ohio riverfront and highlights numerous historic sites around downtown, including several associated with boxing legend Muhammad Ali. It then proceeds to Old Louisville, where dozens of beautiful homes date to the 1870s, and to the thriving NuLu district, a hip, artsy neighborhood that is quickly becoming one of the city’s hot spots.
Kentucky Derby Museum
Located adjacent to Churchill Downs, the Kentucky Derby Museum tells the story of America’s most famous horse race. In addition to several floors of exhibits, the museum is also the jumping-off point for guided tours of the Churchill Downs racetrack. After the tour, the FAM group watched an 18-minute immersive film, “The Greatest Race,” then created their own customized Derby hats in the hands-on “Hatitude” experience. They also participated in a HorseTalk session, where an experienced local fan taught them how to read a racing form and place wagers on the evening’s races.
Churchill Downs
Though the eyes of the world turn to the twin spires of Churchill Downs each year on the first Saturday in May for the running of the Kentucky Derby, live Thoroughbred racing takes place at the track from late April through late June and again from late October through Thanksgiving weekend. The FAM group watched twilight racing from posh seating in the Turf Club, where they enjoyed a delicious buffet, classic mint juleps and a picture-perfect ending to their time in Kentucky.
For more information on this tour or planning your own Kentucky itinerary, please contact:
Kentucky Department of Tourism
Chenelle McGee
502-892-3232
