Manhattan on the Rocks: A Prohibition and Speakeasies Walking Tour

New York City's Prohibition era was one of its most colorful and law-defying chapters. On this walking tour through the Lower East Side, Little Italy, and Chinatown, you'll trace how Prohibition transformed a city with roughly 15,000 saloons into a city filled with tens of thousands of illegal drinking establishments. You'll also discover how that same law accidentally invented modern nightlife, the cocktail culture we know today, and a new kind of American woman.

The tour starts at Tompkins Square Park in the East Village, where a Temperance fountain – installed to encourage people to drink water instead of whiskey – sets the scene perfectly. From there, you'll walk through neighborhoods shaped by successive waves of immigration, from the German enclave of Kleindeutschland to Little Ukraine, passing legendary institutions like Katz's Delicatessen and Russ & Daughters along the way.

The route winds through the Lower East Side and into Chinatown's Doyers Street, where you'll discover both modern speakeasy-style bars and The Back Room - one of the rare surviving New York establishments that actually operated as a speakeasy during Prohibition. Hidden behind an alley and accessed through an unmarked entrance, The Back Room was used by gangsters - Meyer Lansky, Lucky Luciano, and Bugsy Siegel - as a meeting spot. You'll hear how the world of bootlegging helped transform American organized crime. The tour ends near Apotheke on Doyers Street's infamous Bloody Angle, an apothecary-themed bar housed in a building long rumored to have once contained an opium den.

On this 90-minute tour, you'll have a chance to:

• Find the discreet entrance to Death & Co., one of the landmark bars of New York's modern craft-cocktail revival
• Enter Beauty & Essex through a functioning pawn shop concealing a grand restaurant behind it
• Learn how Blind Tigers and Blind Pigs used taxidermy exhibits to serve complimentary drinks legally
• Hear the colorful Prohibition-era story of rum-runner Captain William McCoy—and why one popular legend credits him with giving us the phrase “the real McCoy”
• Locate the former home of Milk & Honey, the influential 1999 bar that helped ignite the modern craft-cocktail and speakeasy revival. Today, Attaboy carries on the cocktail tradition at the same address
• Spot the Mietz Building that appeared as the Corleone family's olive oil company in The Godfather

From temperance fountains to hidden bars, bootleggers to bartenders, this is the story of how a law intended to make America sober helped create a new American nightlife. Raise a glass to one of the country's most spectacular legal experiments—and to the nightlife it helped unleash.