From Our Archive
This story was published before Summer 2021, when we launched our new digital experience.

Confessions of a New York Tour Guide

The dream: Becoming a custodian of the city’s secrets and introducing wide-eyed visitors to its majesty and rich history. The reality: Babysitting drunken tourists on double decker buses, ducking branches, and developing a tolerance for electric shocks.


Your Home Decor Deserves a Big Hand


Your Home Decor Deserves a Big Hand

New York City boutique Oroboro offers a uniquely curated collection of homeware,...

Where to Stay on the Left Bank and an Exquisite Ryokan in Japan


Where to Stay on the Left Bank and an Exquisite Ryokan in Japan

Plus, Italy, Boston, and a few stops out west. These are the hotels our editors...

How the Gucci Loafer Became a Modern Icon


How the Gucci Loafer Became a Modern Icon

As its 70 years of illustrious history prove, the style makes a lasting impression.

On the first warm spring day in 2004 I took a walk through Central Park, feeling miserable for myself. I was 29 years old and working a job I despised: harassing people over the phone, hoping to sell them packages of Broadway theater tickets. Wasn't there a job out there for me? As I shambled out the southeast corner of the park (across from the Plaza Hotel, right where you are supposed to have a revelation) one of those red double-decker buses pulled over, letting out a group of happy tourists.

“Aha!” I thought. “What could be better than schmoozing with guests from out of town? I wouldn't have to sell them anything, New York would do that part for me!” I raced up and to the tour guide to ask how I could be just like him, but he didn't want to deal with me. He was smiling his good-byes to passengers that came all the way from Copenhagen, Cairo, and Kansas. Only later did I realize how lucky I was that he didn't sock me in the jaw for interrupting his tip flow.

“Call this number,” he muttered, handing me a brochure. “But you gotta take a test.”

I read the Michelin Green Guide to New York City and went to the Department of Consumer Affairs to take a multiple choice exam on what size vehicles can ride on the West Side Highway, who designed the Chrysler Building, where one might find the birthplace for the first American saint and why Turtle Bay is called Turtle Bay? (The answer isn't what you think.) I scored well enough to pass and my life changed forever. I was an Official New York Know-It-AlI.

Cut to three years later in the NYC tour guide salt mines. I was a pedant with a late-onset obsession of New York's historical and architectural contours. And I was racing down Fifth Avenue's Museum Mile—zooming past the Felix M. Warburg Mansion (now the Jewish Museum), the Andrew Carnegie Mansion (now the Cooper-Hewitt Smithsonian Design Museum), and Frank Lloyd Wright's triumph of modernist architecture, the Solomon R. Guggenheim Museum—when the latest in a series of electric shocks hurt so much I thought my beard was going to catch fire. It was time to get off the bus.

Electric shocks were just part of the deal during winter. I was holding a microphone that felt like an icicle even through two pairs of mittens, but a sightseeing guide in New York is nothing without his microphone. I had the thick, seasonal beard because any protection from winter wind atop the open double-decker is helpful. (My poor female colleagues had to shout their repartee through layers of thick scarves.) This brutal day I was on the bus’s upper deck with a group from Down Under, and hearty Australians, fearless in the face of any weather condition, will never take a tour guide’s hint and ride on bottom deck. And if they were up there, I was contractually bound to be up there with them.

What took me a little while to learn was this: my function as a learned storyteller about the great city of New York had naught to do with imparting wisdom and chuckles to tourists as we slingshotted around the island of Manhattan. The only reason I hadn't been replaced with a CD or a geo-targeted automatic MP3 file was to make sure litigious ticket buyers didn't rise from their seats and whap their heads at one of the dangerous parts of the tour. (Mostly, a low-hanging light on West 34th St near Macy's and by some thick, limbo-ready branches not far from Grant's Tomb.)

By the end of my run I could go on and on about the Colonial history buried beneath the feet of rushing Financial District workers, tell you where to get the best fried dumplings in Chinatown and, most importantly, which hotel lobbies had clean and easily accessible restrooms. (Oh, The Paramount on West 46th, how much do I owe you?) I was also a tiny bit obsessed with the “Skyscraper race” of the early 1930s, particularly between 40 Wall Street, 70 Pine Street and the Chrysler Building, which actually hid its spire inside for a last-minute record-breaking sneak attack. (The Empire State Building would blow them all away in the end.)

In between I learned that New York City tour guides are the hyper-educated heirs to the three-card monte players that once lined the streets of this town.

The ones that did well knew how to improvise. The tour route I had went by St. Patrick's Cathedral and I had a planned spiel—from the architecture to its importance in Irish-American cultural acceptance to Robert Kennedy's funeral—but some days traffic would send us around the back. Luckily I could speak just as enthusiastically about the Leonidis Chocolatier we'd pass on Madison. (And every time I was guaranteed to have some tourists disembark and ask for the precise location again.)

Early on I worked the Night Loop, which, when the weather is right, is still the greatest way to see the city. I'd sneak on friends who lived here for years and they always regretted not doing it earlier. My Night Loop driver was a guy we'll call Andre, a warm, jovial man from the Bronx who, on the first day, asked “Hoffman, are we going to be friends?” I said, “Uh, of course?” and then he reminded me that management had all quit for the day, and the streets were ours.

To ride the Night Loop you had to have a ticket and most bought them from wandering vendors around Times Square, where the circuit began. Andre would be sure to leave before we were loaded, cruise up a few blocks, pull over and start making deals. He'd let anyone on if they had cash, and would start at the same asking price as the company.

Most were clueless tourists, but some would catch on and haggle a bit. I stayed out of the way. I was still in a phase where I thought my insights into Beaux-Arts architecture would blow everyone away. Most people just wanted to ride around up top and feel a breeze and maybe discretely sip a beer. Andre always gave me a wad of cash at the end of the night. “Here's what we got when I went fishing.”

My time on the double-deckers got me a few gigs hosting walking tours, which usually meant accompanying school groups who'd come in on their own bus. I'd take them to the top of the Empire State Building or out to the Statue of Liberty, spouting a few factoids to anyone who cared. The kids from the South were always well behaved. Usually the Canadians were, too. If the group came from Orange County, California, it was what we'd call a “combat tour,” mostly shouting over brats who wouldn't stop talking.

The kids would naturally want to buy knickknacks, and there were certain vendors who'd kick us back a few bucks based on how many we'd bring in. Same with lunch, and there was one of those enormous cafeterias with a hot bar right near City Hall that was the most generous. I'd feel a little bad because the pizza there was about as good as what you'd get at the airport, but there was always seating, plus that buck-twenty-five per head added up. After lunch we'd go to the World Trade Center, which at the time was just a construction site, and I'd answer the same “Where were you?” question each time. I explained that I was home watching on television like everyone else, but my neighborhood in Astoria had an unmistakable, fiery smell for ten days after that I can still recall today.

Only once did a kid ask, “Is it true that some people were warned not to come to work that day?” By and large even the snottiest students felt a degree of awe in the presence of the building's absence. At the time I had a real pet peeve with people calling it “Ground Zero.” It felt too much like branding, and, technically, the term ground zero was already defined as the area closest to an atomic blast. I'd end my little explanation at the site (which included basic facts about the day) with “so please don't go back home and tell people you saw 'Ground Zero,' but the 'World Trade Center site.'” One time after my speech I heard a teacher get on her cell phone and say, “we're just finishing up at Ground Zero.”

The double-decker shifts rarely got you off the bus, and they also meant a good degree of downtime at the dispatch office/brochure distribution center that was a former porno theater featured in Martin Scorsese's Taxi Driver. That's where I got to bond with the raucous group of raconteurs that acted as the frontline of New York City's welcoming face to tourists.

There was Irving, a retired teacher with a hairstyle matching David Ben-Gurion's, who lived out in Flushing and grew his own gross, squishy, tiny tomatoes. He'd bring them in wrapped in aluminum foil and cut them with a plastic knife he'd pilfered from a nearby Burger King. He'd always offer you a slice and one time I was foolish enough to say yes. He'd come back the next day having clearly recycled the same square of foil. But he knew everything about the city, particularly the UN, and often played the harmonica on his tour.

There was Ben, a retired television producer whose goal in life was to tell you what the tabs were at all the dinners he attended. “When I was at CBS you never saw such indulgence!” His knowledge about the city may not have been too deep, but man could he tell a joke, and the people on his bus always had a good laugh. I once witnessed him browbeating the men on his bus not to wait to turn 50 to get a colonoscopy.

There was Chuck, a retired cop who swore up and down that the only show or movie that got the NYPD right was Barney
Miller. There was Jocelyne, a rocker chick with an enormous head of curly red hair who'd tell tales from her years at the Pyramid Club and Danceteria. There was Sammy, a recent graduate of Yeshiva University who interpreted the entire city through the lens of different “Seinfeld” episodes.

There was Ronny, a handsome Italian-American with long black hair who looked like he was a member of the Ramones. His accent was so thick you'd think it was a put-on. He lived in a single room occupancy in Hell's Kitchen with a tub in the kitchen and was obsessed with Alexander Hamilton long before it was trendy. Ronny remains the only person I've ever met who could talk about Federal banking and make it sound completely punk rock.

There was Bill, an ex-late night DJ with a long gray beard who got background work playing homeless guys on shows like Law and Order. He also worked as the stage manager for classical composer Peter Schickele, better known to old school supporters of public television as the creator of P.D.Q. Bach. (He introduced me to the maestro once and we went out for milkshakes.)

There was Allen, who gave every indication of being a card-carrying member of the Communist Party, and had instant recall of historical, geographical and cultural facts about New York City. He knew every architect, every street, every shop, every
former shop, and what show opened at what theater in what year. If ever anyone had a question (and this was before we could whip out our smartphones) we all knew to ask Allen and trust his answer. The punchline was that Allen lived in Jersey.

Finally there was Rich, who stood at well over six feet and was built like a tank. He had the weird habit of greeting riders by asking, “Where are you from?” and if they said “Wisconsin,” he'd recite the names of their last ten governors. If they said “Holland” he'd do the same with Prime Ministers.

Rich's tour was awful. He'd spout off irrelevant facts without taking a breath, mostly about political figures and art history. He had strange vendettas against gallerists and would rant about recent shows even though his bus was nowhere near Chelsea, and a family of five from Britain really just wanted a picturesque ride on the way to the Statue of Liberty. People would get off his bus and wait for the next one to pick them up. I know, because a lot of times it was me. “I hope you aren't just going to shout,” they'd say.

My tour was abundant with facts, but certainly more mellow. Toward the end most of my friends knew that we couldn't walk two blocks in this town without me dropping a bunch of trivia: “This is where Roscoe Conkling died after walking home during the Blizzard of 1888!”


Before I quit I was a man possessed. I had to let these stories out. I preferred the company of people who would get a reference to “Evelyn Nesbit's swing” without context, and abhorred anyone who'd ask anything so lamestream as “Why is New York called 'The Big Apple?'”

There isn't much money in being a tour guide, in addition to getting electric shocks and freezing in the winter, but near the close of my tenure I was an occasional extra hand in the weird tourism offshoot called Destination Management. This meant showing up somewhere when high rollers were coming into town and just making sure things were going smoothly in a world of only flip phones. It was my job to put on a red tie, go to Kennedy Airport, collect people and put them on a bus. I was usually the only man there, the rest were gorgeous young women in a red scarf.

One time all I had to do was accompany the spouses of some visiting international businesspeople from the Marriott on Lexington to Bloomingdale's, whereupon they threw down what was likely a significant percentage of their nation's gross domestic product.

Another afternoon I aided busloads of people onto elevators headed to a top floor of the still uncompleted World Trade Center Building 7. The VIPs were being propositioned to rent space somewhere in the future WTC complex. There were speeches and powerpoint slides, and I hung back by the coffee and dessert because the school group tours didn't offer coffee and dessert. As people mingled by the enormous windows my instincts kicked in.

“That's 70 Pine Street, and that's 40 Wall Street. Let me tell you funny story about that in relation to the Chrysler Building further uptown.” They were interested. Who wouldn't be interested? There are so many great stories about this city. I'm glad I had my turn telling them.


Let’s Keep in Touch

Subscribe to our newsletter

You’re no longer on our newsletter list, but you can resubscribe anytime.