The Roaring 20’s in Kentucky
From Gatsby to Gangsters
4 Days | Spring | Summer | Fall
Starting At $Flexible Pricing
From Gangsters and Riverboats in Newport (Cincinnati) to The Great Gatsby and Speakeasies of Louisville, this tour covers the glamour and intrigue of the Roaring 20s. Discover Kentucky 100 years ago through the classic novel by F. Scott Fitzgerald and one of the nation’s most “spirited” decades.
Highlights
Tour Highlights:
|
Tour Inclusions:
|
U S Tours Flexible Pricing:
- Customizable Comps
- Net Rates
- Luxury or First Class Hotels & Meals
- Motorcoach Transportation & Professional Tour Managers are available
Whatever you want, U S Tours will be happy to structure tour prices to match your needs. Just let us know!
Itinerary
Day 1 – Newport, KY – Riverboat Dinner Cruise
Your tour begins in Newport, KY (the Southside of Cincinnati). It was once notorious for gangsters. Before Las Vegas, Newport was the original “Sin City” filled with gambling, speakeasies, and gangsters. Check into your hotel for an overnight stay.
Then enjoy a two-and half-hour dinner cruise aboard one of the B. B. Riverboats – the Belle of Cincinnati or River Queen. Take in the skyline, watch the river go by and listen to the soft sounds of the DJ and enjoy a fantastic meal. (D)
Day 2 – Newport Gangsters Tour – La Grange Main Street – Cocktail Class – Louisville, KY – Derby Dinner Playhouse
After breakfast you enjoy a Newport Gangster Tour. This immersive experience will take you through the infamous streets where notorious gangsters like Moe Dalitz, George Remus, and Dutch Schultz made their mark.
See the historic buildings that were once home to casinos and brothels. Hear the captivating tales of fortune and downfall that shaped Newport’s past and laid the groundwork for the modern gaming industry. Witness firsthand how this small town’s dark history has become a cornerstone of its vibrant present.
Depart Newport following the tour and stop in La Grange, KY, where you enjoy some free time on Main Street. La Grange was featured in the HGTV series, “Home Town Kickstart” that premiered April 24th, 2022. La Grange is the ONLY town in the world with a CSX freight train running ON its Main Street! It’s called a “Streetrunner!” But you don’t have to be a train enthusiast to love this one-of-a-kind experience of the train passing slowly by while you sit in awe on a park bench on the courthouse lawn. In addition to the train, Downtown has a very walkable Main Street filled with shops, galleries, boutiques, consignment shops, hobby shops, and restaurants.
You then enjoy a Cocktail and Mixology Class with period cocktails inside the historic Gatewood Pharmacy. The perfect interactive tour of the cocktail scene of the mid-19th to early 20th Century and the mixology that went with it.
End the day in Louisville, KY where during the 1920s, infamous gangsters, like Al Capone Lucky Luciano and a Cincinnati mobster named George Remus, “The King of Bootleggers,” frequented. The Seelbach Hotel being a notable location for their activities, including gambling and bootlegging. F. Scott Fitzgerald also frequent this hotel during his brief stint in the area. It’s here Fitzgerald is said to have rubbed elbows with mobsters and bootleggers, one of whom is said to have ultimately inspired the character of Jay Gatsby.
Check into your hotel for a two-night stay. (Those looking for the ultimate Gatsby & Gangster experience, may want to request lodging at the Seelbach Hilton Hotel.)
This evening, your group will enjoy the dinner buffet at The Derby Dinner Playhouse along with a live theatre production. It is a great evening of entertainment. (B,D)
Day 3 – Kentucky Derby Museum w/lunch – Old Louisville Tour – Evan Williams Experience – Speakeasy Dinner w/Entertainment
Start today with a visit to the Kentucky Derby Museum located on the grounds of Churchill Downs. The Museum is dedicated to preserving the history of the Kentucky Derby. You will have access to two floors of interactive permanent exhibits. The Greatest Race is a 360-degree, 18-minute experience that will make your heart race & emotions soar. Lunch is included at the Derby Café.
Then meet a local guide for a tour of Old Louisville. Louisville, as portrayed in The Great Gatsby, is depicted as a city of social status and refinement. On this tour of Old Louisville, see historic mansions and get a sense of grandeur and elegance like high society events depicted in the novel.
Plus, hear stories of bourbon barons, racetrack royalty, and the titans of tobacco who used to reside in the opulent mansions and inviting townhouses on St. James Court and Millionaires Row.
Your next stop today is The Evan Williams Bourbon Experience. Step back in time to meet Kentucky’s first licensed distiller, Evan Williams. The tour starts with an exploration of the Louisville wharf and Whiskey Row, starting in the late 18th century through the present with digital and physical recreations. See the state-of-the-art operating distillery located on-site that utilizes the same type of pot stills used in the early Bourbon making days. Following the tour, sample products from the Evan Williams award-winning portfolio.
End the day with a Southern Style Dinner in the Evan Williams’ Speakeasy. You will be transported back in time to the 1930’s to celebrate the end of Prohibition. Entertainment will also be included with dinner. (B,L,D)
Day 4 – Depart for Home
After breakfast, depart for home. (B)

