Newport "Sin City" Mobster Tour

Overview

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.

City: Kentucky

Fri 31 Oct

Other dates

You can choose the date already on the booking website

Starting at $35.00

Make a reservation

Fri 31 Oct

Starting at $35.00

Make a reservation

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What's Included

Visual Tour Guide

Air-conditioned vehicle

Additional Info

Infants and small children can ride in a pram or stroller
Service animals allowed
Suitable for all physical fitness levels

What To Expect

Wooden Cask Brewery Company

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!

Thompson House

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!

Cancellation Policy

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

Traveler Photos

Reviews (44)

jtwinch1

Feb 2025

Chris the owner of the business (River City Tours) was a very knowledgeable and pleasant person to listen to. Even though I had some awareness and knowledge of certain events he really brought life to it. I would highly recommend this tour. They also have a ghost tour of haunted sites. I think I plan on going to that also. We also really appreciate driving around and discussing history, as opposed to walking so much as we both have difficulty doing that.

590denaeb

Feb 2025

The host is very informative. He took his time and he was very respectful of time. Christopher was a very nice tour guide. And the tour was extremely informative also enjoyable. I recommend it.

musacchiatara

Jan 2025

The tour was a fun way to spend an afternoon. We love mob history and learning of all the local ties from our guide, Chris was very interesting. I’ve lived in this area my whole life and I learned so many stories and facts. Chris was knowledgeable and engaged. We had a fantastic time and learned about Newport, Ky and its deep rooted connection to mob history.