New York: Speakeasy Bar Crawl & Prohibition Stories Tour

Summary

Secret bars, classic cocktails and wild stories in Midtown NYC

You’ll slip through unmarked doors in Midtown New York with a local guide who knows every speakeasy story worth telling. Taste classic cocktails where Prohibition legends once hid out, wander Restaurant Row between stops, and share laughs (and maybe secrets) with new friends before stepping back into the city’s bright chaos.

What’s the experience like?

You know that feeling when you step off the sidewalk and suddenly everything’s quieter? That’s what happened right after we met our guide near Times Square — one second, neon chaos, next thing I know, we’re ducking down a side street toward a door I’d have walked right past. Our guide, Marcus (born-and-raised Queens — he told us twice), just grinned and said, “Trust me.” The first bar smelled like old wood and orange peel. The bartender slid over something smoky and sweet; I tried to guess the ingredients but gave up after the second sip. There were locals in vintage hats laughing at some private joke. It was weirdly comforting.

We wandered Restaurant Row after that, which honestly feels like another planet compared to the rest of Midtown. Lights from Broadway theaters bounced off puddles (it had rained earlier — you could still smell it rising from the pavement). Marcus pointed out where immigrants used to sneak into back rooms during Prohibition. He told this story about a mayor who’d raid bars by day and drink there by night — everyone laughed except this one guy from Texas who just looked confused. At the second stop, I tried to order in my best 1920s slang (“giggle water,” apparently), but the bartender just winked and handed me a gin fizz.

I didn’t expect to feel so connected to strangers over old stories and strong drinks. By the third bar, someone started humming Gershwin under their breath while we listened to how these places survived crackdowns and blackouts. The walls felt sticky with history — or maybe it was just spilled whiskey, hard to tell. Anyway, I still think about that last toast we did under a chandelier older than my grandma. There was something about sharing all those little secrets with people you’ve only just met that stuck with me after we stumbled back out into Times Square’s lights.

Step-by-step itinerary

Day 1 — 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

Top questions

How many bars do you visit on this New York speakeasy tour?

The tour includes visits to three historical and iconic NYC bars or pubs.

Is there food included on the speakeasy bar crawl?

No meals are included, but you’ll walk through Restaurant Row where you can grab food before or after.

Do I need to bring ID for this NYC bar tour?

Yes, participants must bring a government-issued photo ID or passport as proof of age (21+).

What’s the dress code for the New York speakeasy tour?

The dress code is upscale casual—no sportswear or ripped clothing allowed.

Are public transportation options nearby for this tour?

Yes, public transportation options are available close to the meeting point near Times Square.

Is hotel pickup included in this New York bar tour?

No, hotel pickup isn’t included; you’ll meet your guide near Times Square.

What’s included

Your evening includes express entry and preferred treatment at three historical Midtown bars or pubs, guided storytelling about U.S. immigration and Prohibition history from a licensed local guide, plus all admission fees covered along the way.