• Grand Central Terminal - Join the guide inside Grand Central by the main clock. The first destination is a historic speakeasy concealed within the terminal. Uncover how New York’s elite secretly indulged during Prohibition and enjoy intriguing tales of underground parties and high-society nightlife in the 1920s.
• Lower East Side - Take the subway to the Lower East Side and explore one of the city’s oldest tavern-style bars. Discover how immigrant communities and saloon culture influenced New York’s social scene.
• Lower East Side - Conclude the tour at a historic nightlife venue associated with organized crime. Listen to stories about bootlegging operations, mob bosses, and how underground networks sustained the city’s vibrant nightlife.

• Local guide

• Alcoholic beverages
• Gratuities
• Public transportation (bus, subway, cable car, etc.)

Meet your guide beneath the iconic clock at Grand Central Terminal and journey back to the 1920s for an evening exploring New York City’s hidden Prohibition-era nightlife. Trace the paths of bootleggers, mob bosses, and socialites as you discover the city’s clandestine bar scene.

Throughout the tour, visit three historic speakeasies, each with its own tale of secret parties, elite gatherings, and underground drinking. At one location, enjoy some free time to unwind and savor a traditional drink. Drinks are optional and at the guest’s own expense.

Your guide will share stories of Prohibition-era New York, including organized crime, bootlegging routes, and how New Yorkers enjoyed nightlife despite the ban. The tour blends history, true crime, and social storytelling for an engaging, immersive night out.

The tour concludes at a former gangster hangout, unveiling how mob networks influenced the city’s nightlife.

• Guests under 21 years old are not allowed to participate. Please bring a valid form of identification.

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