What Exactly Is New York?

City Hall has some thoughts. So did I.

To most New Yorkers, "the city" refers to Manhattan. The City disagrees. Photograph by Diana Perez.

After years of my mother’s lobbying with the persistence of a community board member, I’m submitting my New Yorker instincts to municipal scrutiny by taking the NYC Sightseeing Guide Exam. I love New York, and am drawn to helping visitors make sense of this palimpsest of a city. Outsiders seem to detect my beacon; I’m often stopped while waiting for the train or walking while minding my business. Usually they ask for directions. Reflexively, I ask for their ultimate destination and provide the answer they’re looking for while adding the one they haven’t asked for but truly need.

Options respect man’s free will. Still, I feel duty-bound to prevent visitors from experiencing the city as rendered in outdated guidebooks. And now, I’ll have a municipal license to do just that. Sure, take the 4 and transfer to the Bx25 or Bx26 to reach the New York Botanical Garden. But why work that hard when you’re already at Grand Central? Take the Metro-North directly to the Botanical Garden stop. By all means, continue down this street for that Starbucks, but it’ll taste the same in SoHo as in your hometown. Instead, walk a few blocks east to Buddies Coffee in Loisaida and savor the flavors of Puerto Rico in a creamy Coquito Latte, hot or iced.

When I signed up for my summer of study, I assumed that, as a lifelong, committed New Yorker, the sightseeing guide exam wouldn’t be that hard. After all, New Yorkers know the subway so intimately that we know which car will leave us closest to the exit we want. Some of us beam with pride at getting our driver’s license in our thirties. And many of us call Manhattan “the city,” even though “The City” consists of five boroughs. Surely that should count for something on the test, right? Wrong. A few sample questions from a practice exam, and I got checked by my own municipal government. Turns out there’s an Official New York to be learned.

150 pieces of municipal arcana + August humidity = brain liquefaction.

To pass, candidates must correctly answer at least 97 of 150 questions, including which famous author hated brownstones (answer: Edith Wharton) or the original name of the Cotton Club (Club Deluxe). In other words: 150 pieces of municipal arcana + August humidity = brain liquefaction. Why can’t they ask for the name of the neighborhood along Washington Street settled by people from the former Ottoman Empire during the Gilded Age? (Answer: Little Syria.) Or which long-gone Yorkville bakery made black-and-white cookies from the day it opened in 1902? (Glaser’s Bake Shop, sadly, now closed.)

Official New York is a baseline. City Hall requires the license so visitors can confidently hire someone with a minimum knowledge of how the city works and how it came to be. Beyond that, a licensed guide can design their own itineraries and charge for their services. So, during a break from my studies, I assembled a daydream itinerary of the New York I’d guide visitors to experience, beginning with Lower Manhattan and New York Harbor.

On your first trip to New York, you’re forgiven for visiting the obligatory stops: the Statue of Liberty, the Charging Bull, the Brooklyn Bridge. But after the second or third trip, what next? Whether you return for business or the kind of pleasure that hits like sticking your finger in an electrical socket, here’s what I recommend, officially or otherwise.

The last time I visited the Statue of Liberty was a few years ago, and only for research. Before that, high school. Suffice it to say, I don’t feel the need to return unless she’s had considerable work done. I do, however, feel an obligation—nay, responsibility—to shepherd visitors toward what to eat and where and when while they’re downtown (all em dashes are human generated).

You, this view, and a panino. Photograph by Diana Perez.

Say you argued with your travel companion and no longer want to make the trip to Liberty Island. Fine: send them on their merry way. Or perhaps Aunt Linda wants you to accompany her to the pedestal for the third time when you’d rather reach the crown. Send Aunt Linda on her merry way, too. (Book official round-trip ferry tickets in advance through Statue City Cruises, the sole authorized provider.) If you’re fine simply seeing Lady Liberty, first head to Pisillo on Nassau between Ann and Fulton Streets. Order their namesake panino (Prosciutto di Parma, porchetta, bufala mozzarella, roasted peppers, arugula, balsamic dressing), and if there’s a vegetarian in the group, get the Vaticano (provolone cheese, roasted peppers). Grab an aranciata or water while you’re at it. Just bring your hunger.

Sandwiches and soda in hand, go to Fulton St. and take the R or W downtown (or walk) to Whitehall St. to the Staten Island Ferry Terminal. Mercifully, the ferry ride is free. Once aboard, park yourself on a bench on the starboard side and spend the next 25 minutes eating your panino while enjoying the view of the harbor, Lady Liberty included at no extra cost. Don’t worry about finishing before you reach St. George. As soon as you disembark, make a U-turn and board the next ferry back. Stay on the starboard side again, but this time relish the views of Governors Island and the approach to Manhattan. Imagine the Dutch taking in the same view when they first arrived. Before that, the Lenape went about their existence in this area for centuries until, well, you know.

Leaving Whitehall, return the way you arrived and get back on the R or W to Fulton St. Walk past Pisillo and up one block until you arrive at the Bar Room at the Beekman. It’s a sumptuous respite from the clamor of the Financial District and my favorite escape after a long day deciphering 19th-century buildings files at the Municipal Archives on Chambers Street. There’s something so New York about sipping a Manhattan while ensconced in a cushy wingback chair, an overblown portrait of Edgar Allan Poe presiding over the room. Poe did live in New York: He wrote “The Raven” while on the Upper West Side and later moved to a small cottage in the Bronx, where his young wife passed away. But Poe is another tour for another day during another visit. The man truly inhabited New York.

If you’re the type who thinks ahead in months and seasons, time your trip around Overstory on the 64th floor of 70 Pine Street. The building, an Art Deco tower that ranked as the third‑tallest in the world upon its completion in 1932, still carries itself with the self‑assurance of that era. Like their reservations, the views from these terraces require planning.

Mind the suggested dress code at Overstory. Leave the flip-flops, take the Jaeger-LeCoultre.

Overstory is a gem. The menu is seasonal, though the signatures are timeless. The Pink Tuxedo (vodka, cherry blossom, vermouth, strawberry, absinthe) is a riff on the classic Tuxedo, named after the wealthy Gilded Age enclave north of the city. There’s also In the Clouds, a silky, clarified milk punch blending whiskey with Earl Grey tea, vanilla, and champagne. Bear in mind the suggested dress code. Leave the flip-flops, take the Jaeger-LeCoultre.

But if you can get reservations or strike gold as a walk-in, take in both Overstory and SAGA, its sister restaurant on the 63rd floor, with 360-degree views that put you among the city’s twinkling lights at night. From the 64th floor, you’re in good company with generations of New Yorkers and visitors who, for nearly a century, stood here, looked out over the city, and arrived at the same conclusion:

Why would I ever consider being anywhere else but right here, right now?