A Prohibition Tour of NYC’s Most Iconic Secret Spots

Courtesy Belmond

Where to imbibe stealthily in the city that never sleeps.

Departures is published by Meredith Corp. and owned by American Express. While American Express Card Member benefits are highlighted in this publication, including through the links indicated below, the content of this article was independently written by the editorial staff at Meredith. Other Departures content paid for by American Express is explicitly marked as such.

“We turned 90 years old on New Years Eve and that’s unheard of for a New York restaurant,” marvels Cynthia Sutherland, Director of Sales & Marketing for midtown institution the 21 Club. “Who's made it for 90 years? That's why Prohibition is so important.”

Surviving Prohibition intact was no small feat for any boozy establishment across the nation. America’s dreadful 13-year-long dry spell brought the entire alcohol industry to its knees, destroying family-run breweries, shuttering neighborhood pubs, sending the country’s top bartenders packing for Europe’s welcoming shores, and inciting a massive surge in violent organized crime. But as any historian will surely tell you, a government ban against drinking didn’t do much to end America’s taste for the devil’s brew. Instead, the enactment of the Volstead Act forever changed the way we drank, giving rise to a brand new type of bar, one far more secretive—and often much sexier—than the corner taverns and gin houses of the 19th century: the speakeasy.

1919’s New York City, much like today’s, was a patchwork of poor working class immigrants and wealthy business tycoons, all of whom were accustomed to their own version of a stiff drink. The city as a whole publicly eschewed the very notion of Prohibition, finding it prudish and hypocritical, a sentiment cemented in 1926 when then New York Representative (and future mayor) Fiorello La Guardia mixed his own potent elixer out of legal low-ABV “near beer” and malt tonic and downed it in front of a press conference inside his congressional office.

Still, the federal government and its army of New York-deployed G-men did their damndest to enforce the law of the land and in-demand bars like 21 Club had to develop creative means of evading raids and forced closure. 

“We're three townhomes: 20, 19, and 17,” Sutherland continues, describing the club’s plot along West 52nd Street. “We rented 19 before, when we were doing illegal things, so we could hide our liquor in 19. Employees would always tell the FBI when they tried to raid us, 'No, we don't have alcohol on our premises.' Because technically we didn't—we rented 19, we didn't own it.”

And when they couldn't talk their way out of things, there was always the Rube Goldberg approach. “We used to have our doorman press a button when they saw [the FBI] coming that would trigger this gadget thing and drop the bottles down to the basement on top of sand and needles,” says Sutherland. “Everybody at the bar had teacups, so they could take their last swig of alcohol and no one would know what was in it.” 

Thanks to sneaky maneuvers like these, a handful of New York City spots managed to stick it out. Some, like the 21 Club, even made a name for themselves during the devastating decade, providing respite for the thirsty starlets and politicians of the Roaring ‘20s and laying the groundwork for the many modern-day neo-speakeasies that continue to shape American cocktail culture nearly a century later. And while slipping through a false phone booth inside a grungy hot dog joint to find a perfectly crafted Manhattan has its undisputed charms, there’s nothing like experiencing the real thing. From posh hotel bars and upscale lounges to mafia-run dives, step back in time at one of New York’s most iconic Prohibition-era destinations.

21 Club

Martin Scott Powell/Courtesy Belmond 

Rumor has it that some 38 speakeasies lined 52nd Street during the 1920s and early 1930s, and chief among these was original proprietors Jack Kriendler and Charlie Berns’s tony 21 Club. The current location opened in 1930, a full ten years into Prohibition, and, as evidenced above, came up with more than a few methods for keeping the authorities at bay—including maintaining a roster of friends in high places.

“The last time the FBI tried to raid us, Mayor Jimmy Walker was down in our wine cellar with his mistress illegally partaking in spirits,” Sutherland recounts. “When they tried to come in, he called the cops and had all their cars towed and that was the last time they attempted. We had him on our side, which was always good because the FBI was so angry they could never get to us.”

These days the polished, nostalgia-strewn bar and restaurant still caters to a see-and-be-seen crowd of celebrities and political movers and shakers as well as everyday folks in pursuit of a top shelf martini and to-die-for pub burger, albeit in a much more above-board capacity. Those interested in a taste of the past, however, can book a private wine pairing dinner inside the same subterranean cellar that once housed Mayor Walker and his partners in crime. Set behind a thick secret door amid tarnished displays of private stock from the likes of Elizabeth Taylor, Sammy Davis Jr., and Richard Nixon, the all-inclusive experience features seven pours from the club’s award-winning 22,000-strong bottle list throughout what promises to be an unforgettable (and hopefully undisturbed) evening.

The Lambs Club at the Chatwal Hotel

Courtesy The Chatwal, a Luxury Collection Hotel 

Several blocks away in Times Square sits the Lambs Club—the restaurant inside the American Express Fine Hotels & Resorts property, The Chatwal—celebrity chef Geoffrey Zakarian's modern interpretation of the swank fraternal society clubhouse lounge that previously occupied the stunning Stanford White-designed neo-Georgian landmark. Today visitors can sip classic cocktails like Aviations and Old Fashioneds while gazing out over West 44th Street from a round booth inside the hotel’s acclaimed second-floor bar or reserve an event in the wood-paneled Stanford White Studio, a dapper, book-lined 600-square-foot studio where the famed architect and other Lambs Club members enjoyed forbidden beverages by the roaring fireplace. Larger functions find a home nearby in the sprawling Club Room, a 1,500-square-foot expanse bordered by a set of covert, Deco-style wine cellars originally constructed to supply the club’s gatherings with tasty contraband.

The Back Room

Troy Hahn/Courtesy The Back Room 

Referred to simply as “The Back of Ratner’s” thanks to its clandestine location behind Ratner’s Jewish kosher dairy restaurant, this dimly-lit Lower East Side mainstay was a popular hangout for notorious gangsters like Bugsy Siegal, Lucky Luciano, Meyer Lansky, and other titans of the underworld. The mobsters ensured a steady stream of booze flowed freely between the Delancey Street establishment and a nearby garage where bootleggers often unloaded their trucks full of swill. In turn, celebrities from all over the world would frequent the speakeasy, rubbing elbows with hitmen over tart Gin Rickeys. Today you’ll find a more gentile, younger set inside, sipping craft cocktails from teacups and beer from brown paper bags (a playful nod to taboos of the past) against a backdrop of tufted velvet couches and vintage textured wallpaper.

Bill’s Place

While not a bar in the traditional sense, this storied BYOB jazz club began life as one of Harlem’s most beloved speakeasies. Located in the basement of a brownstone along Swingstreet, the neighborhood’s infamous speakeasy row, the intimate parlor room has been hosting world-class musicians since the 1920s, including, most notably, a very young Billie Holiday. Back then the party was fueled by bathtub gin and smuggled-in beer, though the homey venue’s current owner, Harlem Jazz King Bill Saxton, kindly asks modern day guests to bring along their own libations.


Courtesy Chumley's  

Soon after opening its doors in 1922, the ground floor of Industrial Workers of the World party organizer Leland Chumley’s handsome West Village HQ transitioned from a private club for union members into a buzzy—and boozy—hub for literary greats like F. Scott Fitzgerald, Ernest Hemingway, and Willa Cather. Unlike other area speakeasies, the hotspot was able to shake off police raids by keeping a few dirty cops on the payroll. This practice evidently led to the of the industry term “86,” as police would tip off bartenders about imminent raids by instructing them to direct their customers toward the exit on 86 Bedford Street while the Feds rushed in through the side door at 58 Barrow Street. 

Today’s customers don’t have to worry too much about getting 86’d, but they do need to remember the number—the 86 welded onto the modest building’s stately green door remains the only exterior signage. Inside the freshly revamped space, reopened in 2016 after a near-decade-long closure, black and white photographs depict star-studded regulars from times past and illuminated book jackets line the wall above overstuffed leather banquettes. A mix of writerly tourists and locals fill the two-room space each night, feasting on seafood plateaus and trading manuscript advice over period cocktails like Ti’Punches, Mamie Taylors, and the ever-festive Sloe Gin Fizz.

William Barnacle Tavern

Courtesy William Barnacle Tavern

Decked out with nautical flair, historic photographs, and a remarkable collection of absinthe, this friendly East Village dive shares its St. Marks Street address with Theatre 80, a former 1920s jazz club that was converted into an off-Broadway performing arts venue in 1964 by its then-owner, Quaker playwright Howard Otway. During construction, Otway ripped out the jazz club’s attached speakeasy, a famously rough and tumble, bullet-riddled mob hangout called Scheib’s Place. Otway’s son Lorcan, who grew up above the theater and bore witness to the discovery of a basement safe filled with beer bottles and two million dollars in gold certificates, was deeply fascinated with the building’s less-than-savory roots. The younger Otway eventually took over the deed, opening the Museum of the American Gangster, a public gallery devoted to his favorite historical subject, on the second floor and turning the theater’s storefront entrance into a Prohibition-inspired saloon. Visitors can now tour the museum for an in-depth primer on all things organized crime before making their way downstairs for a fittingly old-school tipple.

Pete's Tavern

The uber-powerful men behind New York political machine Tammany Hall used to congregate inside this 18th Street hideaway, originally opened in 1829 as the Portman Hotel before brothers Tom and John Healy purchased the corner outpost in 1899 and refashioned it as a tavern. The narrow space’s carved rosewood bar, exposed brick walls, and worn tile floor continued to draw fat cats and intellectuals throughout the subsequent decades—the writer O. Henry, who lived just down the street, is rumored to have penned his seminal The Gift of the Magi while perched at the bar—and avoided Prohibition’s wrath by installing a phony flower shop out front complete with a fake refrigerator that doubled as the barroom door. The flower shop is long gone, of course, to the delight of the many pint-swigging revelers who routinely swarm the bar’s wraparound sidewalk seating on warm summer evenings.

Flûte Bar & Lounge 

Courtesy Flûte

Descending into this midtown Champagne bar, with its plush maroon couches, colorful contemporary paintings, and sleek metallic touches doesn’t exactly evoke images of Prohibition-era debauchery. But pull back the modern facade and you’ll find the dusty remnants of Club Intime, one of the glitziest, rowdiest, and most risque speakeasies in all of New York City. Helmed by brazen nightlife queen Texas Guinan and West Side wise guy Owney “The Killer” Madden, the hidden cabaret was cloaked in red velvet drapery and stocked with illegal drink, scantily-clad showgirls, and a perpetual audience of socialites and scenesters. And while the decor (and entertainment) might have changed over time, Flûte’s patrons can still conjure the bar’s seedy legacy with a signature Intîme cocktail (three different types of Champagne spiked with peppery ginger extract). The menu also pays tribute to its fiery past by displaying Guinan’s headshot beside newspaper clippings detailing the club’s fateful 1929 police raid.