
Classic Nightclubs & Speakeasies of New York Walking Tour
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 7 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Classic Nightclubs & Speakeasies of New York Walking Tour worth booking?
Classic Nightclubs & Speakeasies of New York Walking Tour is a 2-hour experience in New York, United States, from $40 per person. It scores 63 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 7 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 63 / 100
- Rating
- 5/5 (7)
- Duration
- 2 hours
- From
- $40 per person
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
What you get
- No additional charges.
About this experience
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.
What's included
Included
- No additional charges.
Not included
- Gratuities
- Alcoholic beverages
What you'll see and do
Paley Park
The former site of the legendary Stork Club. “New York’s New Yorkiest place.” - Walter Winchell
15 minutes here
Monkey Bar
The stories behind the storied hotel and its bar. Literary giants to celebrities made it their favored watering hole for a reason.
10 minutes here
King Cole Bar
The story behind one of New York’s most celebrated hotel bars and its famed cocktail.
10 minutes here
Fifth Avenue Presbyterian Church
How a house of worship toppled a hotel and hopes for a bar
5 minutes here
The site of the infamous “Swing Street”. Legendary jazz clubs, speakeasies and saloons lined up and down one of New York’s most famous blocks that helped launch the career of legends.
15 minutes here
Radio City Music Hall
The former site of one of New York’s most celebrated saloons where gangsters, politicians and sports icons could be found under one roof.
10 minutes here
Broadway
Our experience will conclude just steps away from a hidden, speakeasy style bar, offering those who wish to continue the experience a chance to raise a glass to NYC nightlife. Guests are free to experience the venue, but the price of drinks/food is not included in the tour.
30 minutes here · Admission not included
Where it starts and ends
Meeting point
New York
Your guide will be holding a RetroMan tour sign at the meeting point entrance.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Returns to the starting point
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Tue, Sat
- Group size
- Up to 10 travelers per booking
- Operated by
- RetroMan Tours
Know before you go
- 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
Photos






What travelers are saying
Outty’s summary of the themes that recur across 7 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
5 mentionsReviewers describe the commentary as informative rather than scripted.
The guide
2 mentionsTravelers single out the guide as the reason the experience works.
Traveler reviews
7 verified traveler reviews for Classic Nightclubs & Speakeasies of New York Walking Tour. Ratings and reviews provided by Viator and Tripadvisor.
It’s sinatras world we just live in it
What 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 !
via Tripadvisor
Terrific tour
Wow, Andrew really knows his stuff. I learned so much and I consider myself a New Yorker. He is entertaining and informative. Might take again!
via Tripadvisor
An experience to remember!
I 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.
via Tripadvisor
Fun and informative tour
Really 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.
via Tripadvisor
Toots Crawl
Andrew 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.)
via Tripadvisor
Good to know
- Duration
- 2 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- 16+
- Availability
- Bookable today
- Runs on
- Tue, Sat
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 2
- Verdict
- Solid Choice
Why this scores 63
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Classic Nightclubs & Speakeasies of New York Walking Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for New York.
How much does Classic Nightclubs & Speakeasies of New York Walking Tour cost?
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Prices start at $40 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in New York usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Classic Nightclubs & Speakeasies of New York Walking Tour take?
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Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in New York is not rushed.
Is Classic Nightclubs & Speakeasies of New York Walking Tour worth it?
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It holds an Outty Ranking of 63 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 7 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in New York, and how flexible the cancellation terms are.
Can I cancel or reschedule Classic Nightclubs & Speakeasies of New York Walking Tour?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Classic Nightclubs & Speakeasies of New York Walking Tour suitable for kids and families?
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The operator sets a minimum age of 16. Older children generally do well here, and families should factor in the 2-hour running time when deciding.
How far in advance should I book Classic Nightclubs & Speakeasies of New York Walking Tour?
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Around 2 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in New York can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in New York and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.
Where does Classic Nightclubs & Speakeasies of New York Walking Tour start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central New York within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in New York?
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New York has more bookable experiences than any other city on Outty, and the quality spread is brutal. Observation decks are commoditised, so we score them on timed-entry reliability and sunset slots. Food tours and borough walks are where the ranking really separates operators, and the top scores in the city all come from small-group guides. On Outty we rank every New York experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Grand Canyon VIP Helicopter Tour, Half-Day Bus Tour of NYC Top Highlights, NYC Bus Tour of Brooklyn, Bronx, Queens: Art, Food & Sports. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit New York?
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September to early November, and late April through June. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in New York?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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