NYC Speakeasies & Prohibition History Tour with Tastings

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Free cancellationExcellent quality

1/39

Duration3h

GroupUp to 20

LanguagesEN

Mobile ticketAccepted

Three Hidden Bars, One Night, and the Stories Behind Prohibition in Midtown

You visit three historic speakeasies near Times Square with a local guide who walks you through Prohibition-era and immigration history specific to each location. Tastings are included at each bar, entry is express (no lines), and the group stays under 10 people. Bring a photo ID, dress upscale casual, and plan for a few hours on your feet moving between venues in Midtown.

Step-by-step itinerary

Explore NYC's historic bars and landmarks

Walk down Restaurant Row
Visit hidden bars in Restaurant Row
See the lights and pageantry of Times Square
Hear stories of immigration and Prohibition Era

The Experience

The first speakeasy door doesn't look like much—just a unmarked entrance wedged between a chain restaurant and a souvenir shop on Restaurant Row. Your guide knocks, you step through, and suddenly the noise of Times Square disappears. That shift from the street chaos into a dim, wood-paneled room with a working bar is the whole point of this tour, and it hits different when you're not expecting it. You're moving through three of these places in one evening, each one with its own layout, its own drink menu, and its own piece of New York's underground history during Prohibition and the immigration waves that shaped the city.

The guide—a local who knows these neighborhoods like they know their own apartment—walks you down Restaurant Row first, pointing out the architecture and the stories baked into the blocks themselves. You'll hear about the Italian and Irish immigrants who ran these places, the cops who looked the other way, the way a speakeasy worked as both a business and a refuge. It's not a lecture; it's more like someone who lives here telling you what actually happened on these streets and why the bars still exist the way they do. The Prohibition Era stuff isn't abstract—it's tied to the specific buildings you're standing in front of, the names carved into the history of the neighborhood.

At each of the three speakeasies, you get express entry and preferred treatment, which means no waiting in line and no awkward standing around while the bartender figures out what to do with your group. The mixology is real—these aren't tourist traps with neon signs and fake history. You're tasting drinks made by people who know what they're doing, and the guide explains what you're drinking and why it matters to the story. The whole thing takes a few hours, and you move at a pace that lets you actually absorb the place instead of rushing through it like a checklist.

You'll need a government-issued photo ID or passport—they check at every stop, no exceptions—and the dress code is upscale casual, which means no sportswear or ripped clothing. Groups max out at 10 people, so it stays intimate enough that you can actually hear the guide and talk to the other people on the tour. If you've got spinal issues or cardiovascular concerns, this one's not the right fit because you're on your feet moving between venues and climbing stairs in older buildings. But if you're looking to understand a specific layer of New York that most tourists miss, and you want to do it with someone who actually knows the neighborhood, this is the way to do it.

What’s included

Your evening includes a local, licensed guide who leads you through Restaurant Row and three historic speakeasies.
express entry and preferred customer treatment at each venue so you skip lines.
cocktail tastings at all three bars.
and detailed storytelling about Prohibition-era New York and the immigration history of the neighborhood. Public transportation is available nearby if you need it to get to the starting point.

Good to know

Moderate physical levelPublic transport nearbyNot for heart conditionsNot for back problems

Operated by Telltale Tours

Is this one for you?Book this if you want to understand a specific layer of New York's history—Prohibition and immigration—through the actual places where it happened, guided by someone who knows the neighborhood. The small group size and express entry mean you're not herded through tourist-packed bars; instead, you're moving at a pace that lets the stories land.