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Gangster Cool with Roaring ’20s Tours

Call it a paradox of history: Prohibition made liquor sales illegal throughout North America in the 1920s, and yet that decade earned a reputation as one of the wildest times of the 20th century.

Though few of us today are old enough to remember that time, the so-called Roaring ’20s captivate our collective consciousness. Flappers, speakeasies and gangsters have become favorite fixtures in pop culture.

Traces of the 1920s remain in cities all throughout North America, where history has preserved some of the most celebrated speakeasies and colorful characters. Today’s travelers can get a dose of ’20s history and maybe even a taste of a Prohibition-era libations on special city tours and museum visits that showcase the legacy of the Roaring ’20s.

Liven up your group’s next visit to one of these cities by including an immersive historic experience.


Downtown Sacramento Speakeasy Tours

Sacramento, California

If you don’t associate Sacramento with underground revelry during the 1920s, it’s only because you haven’t heard the full story of this California city’s colorful past.

“Sacramento was the wettest city in the nation during Prohibition,” said Shawn Peter, who guides the Downtown Sacramento Speakeasy Tour on behalf of the Downtown Sacramento Partnership. “It had more organized crime than any other city. It was as far as you could be from Washington, D.C., and California didn’t want anything to do with Prohibition because of the beer and wine industry here.”

Even in the early 20th century, the beer and wine industry wielded enormous power in the state. Before he became famous as novelist Mark Twain, Samuel Langhorne Clemens worked as a journalist at a newspaper in Sacramento and reported that the city had more than 200 saloons.

When Prohibition took effect in 1920, most of those saloons turned into speakeasies, and alcohol purveyors used the city’s system of subterranean tunnels to smuggle their goods to the drinking establishments.

Peter’s speakeasy tour is a two-hour pub crawl that visits several sites known to have operated as illicit saloons during Prohibition.

“We start at the River City Saloon to give people an idea of what a saloon would have looked like just prior to Prohibition in a dusty Old West town,” he said. “We go downstairs into an excavated area below grade to an underground tasting room to talk about the wine industry in California. We also visit the Delta King and talk about the boat system. Because of maritime law, once your boat was away from port, you had your own law, so party boats used to travel between Sacramento and San Francisco.”

At each stop along the way, today’s riders on the Delta King get to sample a Prohibition-era cocktail that originated due to the low quality of liquor being served in speakeasies.

“The alcohol they were producing was really bad stuff to drink, so people started coming up with things like Tom Collinses, old-fashioneds, and rum-and-Cokes.” said Peter.


Roaring ’20s Trolley Tour

Atlantic City, New Jersey

If you’re a fan of the television series “Boardwalk Empire,” you know that Atlantic City enjoyed a golden age of sorts during the 1920s, when mob bosses frequented the area, casino gaming was booming and speakeasies were popular establishments around town. Groups visiting Atlantic City today can get a look at the destination of that era by taking the Great American Trolley Company’s Roaring ’20s Tour.

“We’ve designed a tour that highlights the entire island that Atlantic City is located on,” said Stephanie Adelizzi, the company’s director of marketing and sales. “We illustrate the entire island as we drive around the city. We start in Gardner’s Basin, which was notorious for rum runners, and see old boathouses owned by Al Capone and other gangsters.”

The tour continues around the island, stopping at places that were well known during the ’20s. Each participant gets a booklet that shows the area during that period so they can get a picture of how the city looked then.

The tour stops for lunch at the Irish Pub, which was known more for its drinks than its food back in the 1920s.

“It used to be the old Elwood Hotel, and they held a lot of speakeasy parties there,” Adelizzi said. “It still gives you that speakeasy feel, with low ceilings and dim lighting. They have a lot of photos from the 1920s there on the wall.”

From there, the tour continues to several other hotels in the area that hosted speakeasy parties and clubs, as well as Steel Pier, an amusement area on the boardwalk that was popular in the 1920s for its live entertainment.

In addition to seeing a lot of Atlantic City landmarks, guests learn about numerous gangsters that were famous for the techniques they used to work in the area.

“It was known that a lot of the gangsters would do business in the ocean,” Adelizzi said. “They would stand about ankle deep in the water because the ocean noise washed away the sound of their conversation. They never had to worry about anyone hearing what they were saying.”


Brian Jewell

Brian Jewell is the executive editor of The Group Travel Leader. In more than a decade of travel journalism he has visited 48 states and 25 foreign countries.