Kentucky , USA

Newport "Sin City" Mobster Tour

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(57 reviews)

For a full refund, cancel at least 24 hours before the scheduled departure time.

Instant confirmation

Mobile or paper ticket accepted

About this experience

Are you a fan of The Godfather? Goodfellas? Scarface? The Sopranos? The Untouchables? Casino? Boardwalk Empire? A Bronx Tale? If you love mobster movies, then this is the tour for you! This is the only tour about the "Sin City" years of Newport 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.

Available options

Newport "Sin City" Mobster Tour

What's included

Visual Tour Guide

Air-conditioned vehicle

Detailed itinerary

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 New York Syndicate and the famous celebrities who performed there!

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.

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!). You will learn about the indictment and conviction of one of Newport's most notorious mobsters, and how prostitution fueled the local economy.

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!

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.

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.

We will visit Pompilio's Italian restaurant, former home of Colonel Pomp's tavern and an illegal Speakeasy, where you will learn about some mafia rituals and about the restaurant's connection with a famous Hollywood film from 1988.

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!

What's not included

Lunch

Bottled water

Available languages

Guide guide

Written guide

Reviews breakdown

Viator 4.9

19 reviews

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4★

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1★

Tripadvisor 4.7

38 reviews

5★

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1★

Important information

Infants and small children can ride in a pram or stroller

Service animals allowed

Suitable for all physical fitness levels

Meeting point

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.

Important notes

Please show your ticket on your mobile phone or your printed ticket to your tour guide promply upon arrival. Please arrive at your tour starting point 10 minutues prior to your tour departure time.

About Kentucky

Kentucky is renowned for its rolling bluegrass pastures, thoroughbred horse farms, and bourbon distilleries. It offers a unique blend of natural beauty, rich history, and vibrant culture, making it a compelling destination for travelers seeking both relaxation and adventure.

Top Attractions

Churchill Downs

Home of the Kentucky Derby, this iconic racetrack offers a glimpse into the state's rich horse racing history.

Historical/Entertainment 2-4 hours Moderate

Mammoth Cave National Park

The world's longest known cave system, offering guided tours through stunning underground landscapes.

Nature Half-day to full-day Moderate

Kentucky Bourbon Trail

A collection of bourbon distilleries offering tours and tastings, showcasing Kentucky's signature spirit.

Cultural Full-day to multi-day Moderate to Expensive

Must-Try Local Dishes

Hot Brown

An open-faced turkey sandwich topped with bacon, tomatoes, and Mornay sauce, then broiled until bubbly.

Lunch/Dinner Contains dairy and meat.

Bourbon Ball

A chocolate-covered candy made with bourbon and cream cheese, often rolled in nuts.

Dessert Contains dairy, nuts, and alcohol.

Popular Activities

Hiking in Mammoth Cave National Park Horseback riding in horse farms Bourbon tasting Spa treatments Visiting museums Attending live performances Kayaking on the Kentucky River Indoor shopping and dining

Best Time to Visit

Spring (April to June) and Fall (September to October)

Spring and fall offer pleasant weather, making it ideal for outdoor activities and exploring the state's natural beauty. The fall foliage is particularly stunning.

15-30°C 59-86°F