Classic Nightclubs & Speakeasies of New York Walking Tour
Overview
Available languages
2 hours
Mobile ticket
On this immersive walking tour, you’ll wander through the shadows of iconic locations, peeling back the curtain on a vanished world of smoky speakeasies, saloons, storied hotel bars, nightclubs, and jazz joints that made history. We bring to life the characters, cocktails, scandals, and cultural revolutions that made this city swing. Walk the footsteps of jazz greats along the famed Swing Street. Discover the secret back rooms and whispered passwords of Prohibition’s elite speakeasies. Hear tales of café society, gangsters, gossip columnists, and the sports legends and celebrity icons who held court at larger-than-life nightspots. Learn about the cocktails that put these destinations on the map. Whether you're a jazz lover, history buff, or cocktail connoisseur, this tour offers a rollicking ride of New York’s legendary nightlife. Our experience will conclude just steps away from a hidden, speakeasy style bar, offering those a chance to raise a glass to NYC nightlife.
Additional Info
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Suitable for all physical fitness levels
What To Expect
Paley Park
The former site of the legendary Stork Club. “New York’s New Yorkiest place.” - Walter Winchell
Monkey Bar
The stories behind the storied hotel and its bar. Literary giants to celebrities made it their favored watering hole for a reason.
Options
Classic Nightclubs & Speakeasies of New York Walking Tour
What‘s Included
No additional charges.
Gratuities
Note, this is not a pub crawl. We will be discussing the history of cocktails. Our guide will be happy to direct you to drinking locations at the conclusion of the tour.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
7 reviews
Total reviews and rating from Viator & Tripadvisor
It’s sinatras world we just live in it
herbertkB7888AM,Apr 21, 2026
- Review from Tripadvisor
5.00What a fun and educational afternoon Andrew is so funny and entertaining. This was exactly the experience I was hoping to share with my daughter learning about the origins of mt favorite music. My 17 yr old even said it was fun which is no easy feat. I highly recommend this to both locals and tourists !
Terrific tour
G4093BEellens,Jan 18, 2026
- Review from Tripadvisor
5.00Wow, Andrew really knows his stuff. I learned so much and I consider myself a New Yorker. He is entertaining and informative. Might take again!
An experience to remember!
ericahZ6575AQ,Oct 20, 2025
- Review from Tripadvisor
5.00I took RetroMan’s Nightclubs and Speakeasies tour. Our guide, Andrew, was energetic, and so passionate about the material, that he drew us all into the stories of yesteryear. He used a mix of archival photos, music, and visits to several key sites, to really bring the past to life. This was not a walking tour. It was an experience! Highly recommended.
Fun and informative tour
G4093BEellens,Oct 17, 2025
- Review from Tripadvisor
5.00Really wonderful tour of the history of speakeasies and clubs in Midtown Manhattan. Tour guide New so much with great detail and a wonderful presentation. Recommended highly.
Toots Crawl
stevenhJ6242AB,Oct 15, 2025
- Review from Tripadvisor
5.00Andrew provides a true insider's look into the New York City of yesteryear. The tour is a slice of nostalgia as it relates to Manhattan nightlife and all its storied reputation. Indeed, a time when folks would dress up for an evening out - men decked out in jackets and ties, women dolled up in dresses and pearls. Sinatra & Gardner, Bogart & Bacall, DiMaggio & Monroe all make an "appearance" in one's mind throughout the tour. Who better to take us on this illuminating and entertaining journey than Andrew. Not merely trivia, with period photographs and well researched anecdotes and accounts, he demonstrates a passion for the subject matter and allows this fully come through on the tour. My family and I thoroughly enjoyed the 120 minutes and enthusiastically recommend it! Cheers!!! (P.S. Oh, and stay tuned for the conclusion of the tour to find out who this Toots is.)
A tour in the neighborhood
L9235VAtimothyc,Sep 29, 2025
- Review from Tripadvisor
5.00I have worked in midtown for many years, even enjoyed a drink or two in the selected locations. Much of the area was familiar for walking but what a wonderful way to spend a couple of hours hearing about the history of the speakeasies right in our neighborhood. A great tour of midtown NYC Speakeasy bars where the elite used to hang out. All of the nooks and crevices hold stories of the past that are released through RetroMan's enthusiastic and expert story telling. Highly recommended.
Joyful wander down a luxuriantly booze-soaked memory lane or two
clivep601,Sep 25, 2025
- Review from Tripadvisor
5.00You can almost smell the cigar smoke, hear the table talk, and taste the martinis from Andrew's marvelous journey into New York's golden age of bars and backroom nightspots. The ghosts of 52nd Street are brought boisterously to life!
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Operated by RetroMan Tours