NEW YORK GUIDED TOUR FIELD GUIDE
Speakeasy Shadows: A Two-Hour Stroll Through New York’s Prohibition Underworld
A guided, two-hour walking tour that traces hidden speakeasies, Hollywood homes and the city’s political underbelly while you sample Prohibition‑inspired cocktails.
Speakeasy Shadows: A Two-Hour Stroll Through New York’s Prohibition Underworld.
Step back into the Roaring ’20s on a focused, two‑hour walking tour of New York’s secret nightlife. You’ll move through historic streets to uncovered speakeasies and underground haunts, hear stories of bootleggers and citywide corruption, glimpse the homes of Hollywood legends, and stop for era‑inspired drinks at each location.
Highlights
Outing Highlights
Hidden Speakeasies and Underground Haunts
Visit the concealed sites where secret bars once thrived and learn how bootleggers and rebels kept the party going through Prohibition.
Politics, Corruption and Power
Discover how a powerful political organization influenced the city’s underground world and the wider web of corruption tied to the illegal alcohol trade.
Prohibition‑Inspired Cocktails at Each Stop
At each stop you’ll enjoy a drink inspired by the era—an evocative way to connect the historical narrative to what nightlife felt like in the 1920s.
What the day feels like
What the Tour Feels Like
The tour moves at a walking pace through historic neighborhoods, stopping at multiple former speakeasy sites, the homes of Hollywood figures from the era, and locations tied to political power brokers; at each stop you’ll hear era stories and share a Prohibition‑style drink.
Suitability
Who it's for
Who this tour is right for — and who should look elsewhere.
Practical planner
Details to review before reserving
The tour lasts approximately 2 hours.
Comfortable walking shoes, a valid ID for guests who wish to enjoy alcoholic beverages, and weather‑appropriate clothing.
Meet at 7 E 7th Street, New York, NY 10003 for the tour start.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
Do I need to book in advance?
Yes. The operator recommends booking early to secure your spot, especially on weekends.
What if I have dietary restrictions or don't drink alcohol?
Most requests can be accommodated; let the operator know in advance if you have dietary restrictions or do not wish to consume alcohol.
Is the tour suitable for children?
No. The tour is not suitable for children.
How long is the Prohibition Walking Tour?
The tour duration is approximately 2 hours.
Where and when do we meet the guide?
Meet at 7 E 7th Street, New York, NY 10003 at the scheduled tour time.