When I was younger than this (I was never truly young) I started taking guided tours on vacation. For some time, I denied how much I liked them. I wanted to do all the research and reading myself. Then research and reading became my job, and it became a luxury to let someone else do it for me.

It was my first trip to eastern Europe. I was an alt-weekly reporter, working 60-hour weeks for next to nothing. Because it made sense at the time, I sold my car to fund 10 days of travel. But to my body, this was not a vacation but rather a chance to catch up on all the disease it had postponed while I was busy on the job. The prickly-nose feeling started on the plane. By the time I was in the pension in Prague I was filling an Alf-themed trash can with Kleenex and lung tissue. But I really wanted to see Budapest, so the pension owner—from what I now recognize as a social distance—recommended I sign up for the day trip bus tour, which was practically no-effort.
The other 19 retirees on the bus and I had a perfectly nice time, learning about the saints of the city and its politics and the marginalized Roma who live there. I bought all the communist-era cigarettes I could get my hands on during the mercifully brief periods in which I had to walk. Our guide, I think her name was Janet, had a peculiar way of opening each historical explainer with a dramatically drawn-out “In this aaaaaaaaarea …” rolling her R’s and directing our attention with large balletic hands and thereby entering the lexicon of travel phrases permanently stuck in my head.
The bus tour, while not the most exciting, was a good way to learn a whole lot in a little bit of time. With lunch provided! I fell in love with the concept of a single intense day of the tour bus life. Though my mind can be a sieve when it comes to historical facts, I always love to hear good stories, so the pedigree of the guide matters little to me, as long as they’re local and compelling and give good pub recommendations. I started using guided tours for orientation to a place. I’ll ask the hotel for the lesser-known recommendations, or the free city tours, or the student-led themed walks.
I’ve taken some good ones, and some bad. I was completely terrified by a night-time cemetery tour in Charleston, its harbor the entry point for 40 percent of all enslaved Africans and where the Civil War began with shots fired at Fort Sumpter. The Stonehenge tour was mostly an expensive bus ride to Stonehenge. Chicago’s incredible free city walking tours are the world’s best travel bargain by a long shot. In Spain, I took a day tour from Seville to Valencia, and these were among the very few sacred hours I spent away from my family while I was reporting the stories of my first book.
I’m here in Manhattan for a few days. Some family obligations, some work obligations. The tour of Greenwich Village was inexpensive and just long enough. We congregated on an easily navigable corner, as such tours usually do, findable via the requisite Notice Me garb of a tour guide. “You can see this hat from space,” begins Ray, the guide.
I am here on the 400th anniversary of New York. The Dutch East India Company hired Henry Hudson to search for water passage through North America and that’s what started development. While many Americans came to escape persecution, or by force to fuel the industry that made this nation (see: Charleston), the Dutch came to kick out the Lenape Indians and claim all the resources as their own. The Lenape called this island Manahatta, land of many hills, courtesy the soils deposited from glacial activities, as in Iowa. The Lenape had fished the Hudson, farmed the land, and traded oysters in what then became New Amsterdam. This city, in all its iterations, has been about doing business. People came here from all over the world—and England, of course. They brought an armada because it looked like there was a whole lot of money to be had.
Ray whips out his binder of laminated photos, a staple of the guided tour, and shows us a picture of Wall Street, named for the wall built by the Dutch colonists to keep out the Lenape, and of Trinity Church, once its tallest building, to reiterate how much the city has grown since those New Amsterdam days.
We pause at MacDougal Street and learn the story of Gertrude Vanderbilt Whitney, who tried to sell her art collection to the Met. When they turned her down, she built her own damn museum.
Ray gives us interesting pointers we can continue to use, including something that I should have known long ago but didn’t—all brown street signs mean it is a historic area (“In this aaaaaaaaarea …”). We pass the Washington Square Hotel, where Gertrude Stein and Hemingway lived, and Fleetwood Mac once stayed. This is fitting, because I would see Stereophonic the next day (10/10, would recommend.)
In Washington Square Park across the street, Buddy Holly taught guitar for free. Here, the Lenape farmed tobacco, and many of the city’s residents moved here during a cholera outbreak of 1832. As a result, about 20,000 people are buried under this park, and every construction project seems to turn up another burial vault, cemetery, or random coffin. So say hello to the ghosts when you pass under the arch.
Edward Hopper painted Nighthawks “right over there,” Ray says, pointing to some row houses now owned by NYU at Washington Square North. We go under the arch (originally made from wood and plaster) now the unofficial gateway to Greenwich Village. Harry first met Sally here! Good thing the double decker highway didn’t come through like Robert Moses wanted in the 1950s, Ray says. It would’ve cut this arch right in half. (I gaze over at my enormous copy of The Power Broker as I write this; I still have not read it, though it seems to be recommended by every New York media writer.)
Last time I opened this many history tabs on my phone was in Portugal, for opposite reasons. That tour guide’s stories just felt generally wrong—which you’ll remember I have no problem with, but they were also not entertaining. I eventually found out the usual guide was out sick and his fill-in was his brother-in-law. He ended the day with his head in his hands, sitting behind the wheel of the bus, his final announcement to us a defeated “I’m sorry for everything.” Big tip for that guy. Another phrase for the books!
The emergency vehicles in Manhattan are obnoxiously loud, and they interrupt Ray several times. He adds a sidebar that the city had to raise their volume with the advent of cell phones.
Absent today in Washington Square Park is the piano man, who rolls in a grand piano regularly and performs most any song you want to hear. Ray tells us this as we pass the fountain that is not featured in the show credits for Friends. That one’s in Burbank.
Ray points out a brown NYU building that served a former life as the Triangle Shirtwaist Factory. The sweatshop employed mostly immigrant women who spoke little or no English, and locked all doors but one at night, so workers could have their pockets checked to prevent theft. On March 10, 1911, a fire broke out, and though an operator tried to call up to the working floors to warn them, doors remained locked and many who fled were trapped in elevators or plummeted to their death. The building burned in less than a half-hour. The tragedy began the roll of labor-law change.
We move on and pass this music:
And this music:
And I just can’t ever get over how much everything this city holds. Soon I’m standing outside Cafe Wha?, owned by David Lee Roth’s uncle, who you can either curse or thank, depending on where you stand on the Van Halen issue. In the ‘60s, Jimi Hendrix played here when he was still calling himself Jimmy James and fronting the Blue Flames. They played five sets each night, sometimes six days a week.
We pause at the corner of Bleecker & Cornelia streets, where only a small throng of Swifties is gathered today. The rest of us are into Murray’s Cheese Shop, which has me thinking about how hungry I am, and Ray’s voice turns from amusing tales to something something something … 30,000 speakeasies … something something something … 86 Bedford Street, so the term “86 the liquor” started in this neighborhood …
The last time I tuned out like this was during a free ghost tour in Edinburgh. Right off the bat, the guide asked our group of about 20 about everyone’s great fear. What kind of invasive question is that? I was in this to hang in back and get scared in relative peace. We then went through all 20 answers. This killed about a half-hour before we even started walking in the underground vaults. I dug deep for an answer superficial enough to maintain anonymity but complete enough keep things moving, because if you didn’t answer to his satisfaction, this guy asked follow-ups. So here was mine: Losing my glasses while traveling and being unable to access replacements. And the moment I said that out loud, I realized just how often I actually do worry about losing my glasses. It wasn’t a great ghost tour, though our guide inexplicably wore a cape. But I did learn something about myself that day (cue dramatic wrapping-up music).
In Greenwich Village, we pass the Friends apartment and the Ghostbusters firehouse. But I’m more interested in milking Ray for lunch recommendations. Next time you’re in the city, I recommend Buvette, which is allegedly a Jonas Brothers favorite. Best chicken salad I ever did have.
Happy long weekend. Maybe book a tour wherever you are. Always worth it, even if they’re terrible.