Exploring New York City’s Roaring 20s Gangster Mob Prohibition Pub Crawl

The 1920s were the heyday of Prohibition but, although illegal alcohol was outlawed, that didn’t stop many Americans from imbibing and creating a lively and often notorious underground scene. This was especially true in New York City, where the glamorous stars of the era – Joe DiMaggio, Bugsy Siegel and Al Capone – were part of a mob that helped bootleg beer and booze, while running casinos and speakeasies in the city. Today’s New York City tourists can revisit some of the notable locations of that era through a gangster mob prohibition pub crawl.

This is more than just a pub crawl – it’s an educational and entertaining journey into the seamy underworld of New York City in the 1920s. Your knowledgeable tour guide will show you some of the well-known landmarks, buildings and hangouts frequented by the well-known mobsters of bygone days. You’ll sample beers at some of the same pubs and establishments, hear stories about infamous activities, and see the locations where some of the most dramatic events occurred.

Prepare for a Roaring Good Time on the Prohibition Pub Crawl

The Prohibition Pub Crawl takes visitors to several historic downtown locations that give a glimpse into the era of speakeasies, gambling dens, and back alley swindles. The tour is strictly 21-and-over, as you’ll sample some of the same craft beers that were illegal back in the 1920s. You’ll stop at pubs and bars such as Harry’s Bar and Grille, owned by bootlegger John Torrio, who mentored Al Capone; PJ Clarke’s, whose presence in Frank Sinatra’s “New York, New York” made the song even more iconic; and The Financial District, which is filled with prohibition-era stories. Of course, no Prohibition Pub Crawl would be complete without a visit to the busiest speakeasy in town during that time—the historic 21 Club (now just 21).

A Deeper Look at Prohibition-Era New York City

The Prohibition Pub Crawl is an interesting self-guided tour for anyone interested in the history of 1920s New York City. Your tour guide will provide you with fascinating facts and anecdotes about mobsters and their activities during the speakeasy era. You’ll hear stories about the most famous mobsters, learn about notorious activities such as beer-brewing, payoffs to police officers, and scams by police officers.

Along the way, you’ll stop at pubs such as Paddy McGee’s Bar and Grill, where you can explore the explosive history of Irish involvement in organized crime with a beer in hand. You’ll also learn how Jewish mobsters such as Moey Sheik used activities like moonshine brewing to thrive during this period before the repeal of Prohibition in 1933. The tour also stops at various locations that experienced Prohibition crime in their present day operations such as Columbus Park which was known as Boccie ground in those days.

Experience Booze, Booze Related Swag & Games during Prohibition Pub Crawl

Aside from learning about the history of organized crime in NYC during the Prohibition era, you can also sample some craft beers. On the Prohibition Pub Crawl, you will enjoy drinks from several local breweries including Brooklyn’s Sixpoint Brewery and Harpoon Brewery from Boston. You can also expect to taste some of the most popular beers from this time period.

On top of that, each pub stop on the tour has something special planned for tour participants. You will get access to exclusive discounts and gifts such as coasters, postcards and posters, T-shirts with Prohibition-themed designs, themed swag bags with freebies like mugs, hats and other surprises. As an added bonus, games such as Blackjack and Craps will be set up in each pub stop on special tournament nights where winners receive prizes.

Time & Location

The Prohibition Pub Crawl is a leisurely evening event offered most days for about three hours beginning at 7pm. It starts at Mike’s Pizza Bar on Grand Street in lower Manhattan but does not end there (the exact ending location remains a mystery until tour participants arrive). Prices start at just $65 per person with discounts available for groups of 4 or more people.

A Unique Way to Learn About an Unforgettable Time in NYC History

If you want to explore one of America’s most notorious periods while sampling some delicious craft beer, then look no further than the Prohibition Pub Crawl in New York City to enjoy a one-of-a-kind educational experience. It is a perfect way to trace your roots to the era of organized crime while learning firsthand about some of the deeds that earned New York City its infamous reputation during those days. So why not take a moment and book this exceptional tour today right here? You will have an experience that you won’t soon forget!