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NYC Speakeasy Bar Crawl: 3 Historic Bars & Midtown Walking Tour

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Free cancellationExcellent quality

1/10

Duration3h

GroupUp to 20

LanguagesEN

Mobile ticketAccepted

Three Speakeasies, One Night: How NYC's Prohibition Bars Still Pour

You walk between three historic bars and hidden speakeasies in Midtown with a local guide who gets you free entry and skips the lines. Along the way you see Times Square, Roosevelt Island views, and the Theater District while learning how Prohibition-era drinking actually worked in New York. Cocktails are $18–$25, and the group is small enough that you actually connect with other travelers and the bartenders.

Step-by-step itinerary

Visit historic bar and speakeasy
Pass by Times Square
Pass by theater and performing arts area
Pass by Roosevelt Island
View Manhattan Skyline and Empire State Building
Visit Victorian themed bar in Theater District
Pass by West Side Manhattan neighborhood

The Experience

So you're standing in front of a nondescript door in Midtown, and your guide pulls it open to reveal a Victorian-themed bar tucked behind what looks like nothing at all. That's the whole thing right there — this speakeasy bar crawl takes you through three of those hidden spots, the kind of places that don't advertise and wouldn't exist if you weren't with someone who knows the neighborhood. Your local guide handles the logistics: free entry at each stop, no waiting in line, and you're moving between them on foot through the Theater District and the west side of Manhattan, so you're seeing the actual streets where this stuff happened, not just drinking in a vacuum.

The tour threads through Prohibition and immigration history as you go — the bars themselves are the story. You'll hit a historic pub, a speakeasy, another bar, each one with its own angle on how New York drank when it wasn't supposed to. Cocktails run $18 to $25, and yeah, there's a processing fee on top, but you're not hunting for these places solo or negotiating entry with a bouncer who doesn't know you. The group stays small enough that the bartenders actually talk to you, and you'll meet people from everywhere — that's the whole draw of a group night out in the city. Between stops you're walking past Times Square, catching views of the Empire State Building and the Manhattan skyline, and your guide is pointing out the actual history of the neighborhood instead of just moving you from drink to drink.

Dress code is business casual or upscale — no sportswear or ripped stuff — and you need a valid photo ID (passport if you're not American). You've got to be 21. The walking part is real, so it's not a sit-down evening, but it's not a marathon either. Public transit is right there if you need it before or after.

What’s included

Local guide expert in NYC history and culture.
entry to three historic bars, pubs, and speakeasies.
free admission and express entry at each location.
walking tour through Midtown including Times Square, Roosevelt Island views, and the Theater District.
Prohibition and immigration history told through the bars themselves.

Good to know

Easy physical levelPublic transport nearbyNot for pregnant travelersNot for heart conditionsNot for back problems

Operated by NiteTables Experiences

Is this one for you?Pick this if you want to see the real hidden bars of Midtown without hunting them down yourself or waiting at the door — the guide's connections get you straight in, and the small group means you're actually talking to people instead of just drinking in a crowd.