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Duration: 2 hours


A tour of Times Square's sordid past and explore the seedy underbelly of New York City's red light district. Led by a native New Yorker who lived through it all, you'll discover the personalities and places that made Times Square what it was.

🏨 Visit the last remaining hot sheet hotel and live peep show in Times Square

🎥 Discover sites for classic films like Midnight Cowboy and Taxi Driver

🔪 Learn about the most dangerous block in New York City and the dirtiest hotel in America

📷 See graphic vintage photographs that may not be appropriate for all ages


When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.


Practical information

Where does the tour start?
The tour starts in front of the statue of Father Duffy, located on 7th Ave between 46th and 47th St. The statue is at the bottom of the red stairs.

Is the tour appropriate for all ages?
While we strive to make our tours enjoyable for all audiences, this particular tour may not be suitable for young children or those who are easily offended. We recommend that participants be at least 16 years old, but ultimately it is up to the discretion of the parents or guardians.

How long is the tour?
This tour is 2 hours long.

Where does it end?
The tour ends at 50th St. and 8th Ave..

How strenuous is this tour?
This tour is easy and most people can participate.

Is this tour ADA accessible?
The tour does cover a lot of uneven ground, and there are a lot of crowds to navigate. You can email us in order for us to best prepare your visit.

Is this tour mostly indoors or outdoors?
This tour is mostly outdoors.

Full description

Are you ready to delve into the dark, scandalous history of Times Square? Let us take you on a journey back in time to the days when the Great White Way was a red light district, and the Crossroads of the World was XXX-rated. Led by Robert Brenner, a licensed New York City tour guide who spent his youth immersed in the debauchery of Times Square, you'll explore the seedy past of New York City's most infamous district.

From former peepshows and adult book stores to dive bars and sex clubs, we'll visit the places where the demimonde of Times Square once congregated. Along the way, you'll learn about the personalities who made Times Square what it was, from the King of the Peeps to the woman who built a gay and S&M porn empire.

But be warned, this tour is not for the faint of heart. We'll be showing some graphic vintage photographs that may not be appropriate for all ages.

Returns, exchanges and cancellation

Unused Experience Vouchers can be returned within 30 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 72 hours before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 72 hours in advance means losing the value of your experience.

Duration: 2 hours
Regular price $41
$41 Regular price Sale price
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Here's what others have to say!



Based on 0 reviews

Connie T

Great information about the way Times Square used to be in the 70s and 80s. However, although some of the grimy places still exist, a guide is needed to show where they are located. It is recommended to visit these places soon, as they may not be around for much longer.

Patrick T

Our guide, Robert Brenner, was an expert in both social and architectural history. He was able to discuss the roughest and sleaziest times and characters without ever demeaning them or his listeners. His tour was truly informative and interesting, bringing a bygone era back to life.

Mike K

I really enjoyed the tour of Old Times Square. Our guide was very knowledgeable and it was fascinating to learn about the history of the area. I particularly appreciated hearing about the legitimate theaters and the seedy side of Times Square. Although the days of peep shows and porn theaters are gone, it's important to remember the history of the area.