Newport Sin City Historic Sites Tour

While there are a few walking tours about the "Sin City" years of Newport, our tour is the only one where you can view all of the historic sites from the comfort of an air-conditioned vehicle (minivan). This allows us to explore far more historic sites in less time than a walking tour can! You will relax from the comfort of your seat while you are transported from site-to-site and will learn all about the unique history of each site, it's connections with the mafia, illegal gambling, bootlegging, and prostitution that earned Newport the name "the sin city of the south"! You will also have an opportunity to get out of the vehicle at each tour stop and do some exploring of your own, with your tour guide there to answer any questions you may have.

Meeting Point

Wooden Cask Brewing Company

629 York St, Newport, KY 41071, USA

All tours will meet on the sidewalk in front of the Wooden Cask Brewery on York Street. Check-in 5 minutes prior to your tour departure time. Park in the lot across the street from the Wooden Cask Brewery. Please do not park in the brewery parking lot unless you intend to patronize the brewery.

What's included:

• Visual Tour Guide

What to expect:

Duration: 2 hours

Wooden Cask Brewery Company

629 York St, Newport, 41071-1815, Kentucky

We will begin our tour at the Wooden Cask Brewery, former site of the 633 Flamingo Club and learn about its connections with the notorious Cleveland Syndicate mafia and the famous celebrities who performed there, including Marilyn Monroe, Dean Martin, and Frank Sinatra!

15 minutes

eat well celebrations & feasts

518 York St, Newport, KY 41071, USA

We will visit 518 York Street, home of the former Yorkshire Club, one of the largest premiere "carpet club" casinos and perhaps the biggest illegal Horse Racing bookmaking clubs in the 1930's. You will learn about the owner's feud with the mafia and the club's eventual takeover by the mob.

15 minutes

Brass Ass Strip Club

613 Monmouth St, Newport, KY 41071, USA

We will view the exterior of The Brass Ass Gentleman's Club, home of the former Stardust Casino (the Neon star is still on the building!) and Silver Slipper brothel. You will learn about the indictment and conviction of one of Newport's most notorious mobsters, and how prostitution fueled the local economy.

15 minutes

Thompson House

24 E 3rd St, Newport, 41071-1608, Kentucky

We will visit the John Thompson house, home of the inventor of the Thompson machine gun ("tommy gun") and you will learn about how this weapon became a favorite of mobsters in the 1920s and 1930s and its role in the Saint Valentine's Day Massacre!

15 minutes

Gangsters Dueling Piano Bar

18 E 5th St, Newport, KY 41071, USA

We will visit the Gangster's Dueling Piano Bar, site of the former Glenn Schmidt's Playtorium, and you will learn about the owner's feud with the Cleveland Mafia that nearly cost him his life.

15 minutes

Beverly Hills Supper Club Memorial

Southgate, KY 41071, USA

We will visit the historic marker and the Memorial in Southgate, KY, former site of the Beverly Hills Supper Club and the third most deadly night-club fire in U.S. history. You will learn about the troubled history of the club, the owner's feud with the Mafia, and the mysterious circumstances surrounding the fire that eventually destroyed it, killing 165 people in the process.

15 minutes

John Nolan Auto Service

15 E 4th St, Newport, KY 41071, USA

We will visit the John Nolan Auto, former home of Merchant's Club, where you will learn about the notorious mobster who ran the club for the Cleveland Mafia and a gangland shoot-out that nearly led to his death.

15 minutes

Mustang Betty’s Antiques

602 Monmouth St, Newport, KY 41071, USA

We will visit Mustang Betty's Antiques, home of the former Mustang Club where you will learn about a victim of the mob and a mysterious fire where a gruesome discovery was made!

15 minutes