Every time a friend texts me “we’re coming to New York next month” I get a little jolt of panic. Not because I don’t want them here. I absolutely do. But because I know what’s coming next. The screenshot of some list they found online with 47 “must-do” activities that would require them to be in three boroughs at once and never sleep. So I end up typing out the same giant text message every single time. Here it is. The actual advice I give people I care about.
I’ve lived in New York for the better part of a decade now. I moved here with two suitcases and a conviction that I already knew the city because I’d watched every season of Seinfeld. I did not know the city. I didn’t know anything. But I’ve learned. And what I’ve learned is that most of the advice floating around online is either wildly outdated, written by someone who visited once in 2017, or designed to make you feel like you’re failing at vacation if you don’t hit 30 attractions in four days.
So this is different. This is what I actually say, in real life, to people I actually like.
The Stuff I Always Say First
Before anything else, I tell people to slow down. I know that sounds annoying. I know you have four days and a spreadsheet. But the single biggest mistake people make when they visit New York is trying to do too much. You will walk more than you’ve ever walked in your life. Your feet will hurt by 2 PM on day one. If your itinerary has you bouncing from the Upper East Side to Brooklyn to the West Village to Midtown in a single afternoon, you’re going to spend most of your trip underground on the subway feeling frustrated and exhausted.
Pick a neighborhood. Spend the morning there. Walk around. Eat something. Sit on a bench. Watch people. That is the experience. New York isn’t a checklist. It’s a feeling. And you can’t feel it if you’re sprinting between landmarks with your phone out.
The second thing I always say is about shoes. Wear ugly shoes. I don’t care what you packed. I don’t care about your outfit. Wear the most comfortable shoes you own. You’re going to walk eight to twelve miles a day, on concrete, and if you’re in cute boots or new sneakers you will be limping by dinner. I wear beaten-up New Balances every single day and I regret nothing.
Third. Get a MetroCard or set up OMNY on your phone before you get on your first train. Do not be the person holding up the turnstile trying to figure out the machine. The people behind you are late for work and they are not in a forgiving mood. The subway is your best friend in this city. Learn the basic lines. The 1/2/3 runs up the west side. The 4/5/6 runs up the east side. The L goes crosstown and into Brooklyn. The express trains skip stops. Google Maps will tell you exactly which train to take and when.
And the last thing I say before anything else. Don’t eat near Times Square, don’t eat near the Empire State Building, and don’t eat anywhere with a guy standing outside trying to hand you a menu. Walk two blocks in any direction and you’ll find something ten times better for half the price. This city has the best food on the planet, but you have to be willing to walk past the tourist traps to find it.
The Must-Dos That Actually Are Must-Dos
I’m not going to pretend I’m above the classic New York experiences. Some of them are famous for a reason. But there’s a right way and a wrong way to do almost all of them.
Central Park. Yes, you should go. But don’t just walk in from 59th Street, snap a photo of the fountain, and leave. That’s like going to a concert and leaving after the opening act. Enter from the west side around 72nd Street. Walk north. Go past the Lake, past the Ramble (which is this gorgeous wooded area where you genuinely forget you’re in Manhattan), past the Reservoir where you can see the skyline reflected in the water. If you’re there in the fall, the colors in the North Woods section are unreal. The park is over 800 acres. Give it at least two or three hours and just wander. Bring a coffee. Sit on a rock. I promise you it’s better than trying to hit six museums in the same afternoon.
Brooklyn Bridge. Walk it. But here’s my tip. Walk it from Brooklyn to Manhattan. Everyone does it the other direction and you end up stuck behind a wall of slow-moving tourists and people taking selfies in the bike lane (don’t do that, by the way, cyclists will yell at you and they should). Start on the Brooklyn side near the York Street F station or the High Street A/C station. The view of Manhattan getting closer as you walk is one of the best things about this city, especially in the golden hour before sunset. And when you finish, you’re dumped right near City Hall and you can walk to Chinatown for dinner.
The High Line. This is one of my favorite things in the city, but timing matters. Do not go on a Saturday afternoon in the summer. You will be shoulder to shoulder with thousands of people and you’ll spend the whole time trying not to step on anyone’s dog. Go early. Like, 8 AM on a Tuesday early. It’s peaceful, the light is beautiful, and you can actually stop and look at the art installations without someone bumping into you. Enter at the Gansevoort Street end in the Meatpacking District and walk north. It ends up near Hudson Yards around 34th Street. Grab breakfast at Chelsea Market on the way, which is right underneath the High Line around 15th Street.
A Broadway show. Yes, do this. Even if you think you don’t like musicals. There is nothing like live theater in a Broadway house. The energy is completely different from anything you’ve experienced. For tickets, skip the TKTS booth in Times Square (the line is absurd) and use the TKTS booth at Lincoln Center instead, or try the TodayTix app for rush tickets. If you want cheap seats to a specific show, most theaters release a limited number of $30-40 lottery or rush tickets the morning of. It takes some planning but it’s absolutely worth it.
The food. This could be its own article (and it will be). But the quick version is this. Eat a dollar slice. Eat at a halal cart. Get a bacon egg and cheese from a bodega in the morning. Eat dumplings in Chinatown. Get a bagel from a real bagel shop, not a chain. Try Ethiopian food in Harlem. Get tacos in Sunset Park. The best meals I’ve had in this city have cost under $12 and were eaten standing up or sitting on a park bench.
The Things I Tell Everyone to Skip
This is where I lose people. But I’m going to be honest because that’s the whole point.
Times Square. Walk through it once at night to see the lights. Take your photo. Then leave and never go back. There is nothing there for you. It’s a sensory assault of chain restaurants, costume characters who will charge you $10 for a photo, and more humans per square foot than anywhere else on the continent. Every single New Yorker avoids Times Square like it’s radioactive, and there’s a reason for that.
The Statue of Liberty ferry. The official ferry to Liberty Island takes forever, requires advance tickets, involves security lines, and then you’re standing on an island looking at the back of a statue. Instead, take the Staten Island Ferry. It’s free. It leaves from the Whitehall Terminal in Lower Manhattan. It goes right past the Statue of Liberty and you get a gorgeous view from the water. When you get to Staten Island, turn around and take it right back. The whole thing takes about an hour and you’ve just had a better experience than the people who paid $24 and waited in line for two hours.
Most “famous” restaurants. I’m going to get in trouble for this, but a lot of the restaurants that dominate Instagram and “best of” lists are coasting on reputation. I won’t name names here (okay, maybe a few in future posts), but if there’s a two-hour wait and the food is “good,” that’s not good enough. New York has too many incredible restaurants with no wait to justify standing in line for a place that peaked in 2019. The exception is a few spots that genuinely earn their hype, and I’ll tell you about those specifically when they come up.
Hop-on hop-off buses. Please don’t. You’re sitting in traffic looking at buildings through a dirty window. Take the subway. Walk. Take the M14 bus across 14th Street if you want a scenic bus ride. But the tourist buses are slow, overpriced, and you will feel silly on them. I say this with love.
The Empire State Building observation deck. The line is genuinely punishing. If you want a view of the city, go to Top of the Rock instead (you can actually see the Empire State Building from there, which is better than being on top of it). Or better yet, go to the Edge at Hudson Yards if you want the dramatic glass floor experience. But my actual favorite view? The rooftop bar at Westlight in Williamsburg, Brooklyn (111 N 12th Street). Drink in hand, skyline across the river, no line, no $40 admission fee.
The Stuff Nobody Puts on Lists
This is the part I care about the most. These are the things that made me fall in love with New York, and none of them show up on the first page of Google.
The Cloisters. This is my number one recommendation for anyone who has more than two days in the city. The Cloisters is a branch of the Met, but it’s all the way up in Fort Tryon Park at the northern tip of Manhattan. It’s a reconstructed medieval monastery filled with tapestries and gardens and stone archways, and it sits on a hill overlooking the Hudson River. It feels like you’ve left the city entirely. Take the A train to 190th Street and walk through Fort Tryon Park to get there. The park itself is one of the most beautiful green spaces in the city and almost nobody talks about it. I have sent at least twenty friends here and every single one has texted me afterward saying it was the highlight of their trip.
The West Side Highway path. There’s a bike and pedestrian path that runs along the entire west side of Manhattan from Battery Park all the way up to the George Washington Bridge and beyond. On a nice day, walking or biking this path is one of the most peaceful things you can do in the city. You’ve got the Hudson River on one side and the city on the other. There are little parks and piers along the way. Pier 46 near Christopher Street has a great lawn. Pier 25 in Tribeca has a playground and mini golf. I walk a stretch of this path almost every week and it never gets old.
A random comedy show. Not a big ticketed show at a famous club. I mean a Tuesday night show at a place like the Creek and the Cave in Long Island City (it’s technically closed now but the spirit lives on at other spots) or the Comedy Cellar’s late show on MacDougal Street, or Eastville Comedy Club on the Lower East Side. New York has more working comedians per capita than anywhere on earth, and on any given night you can see someone who’ll be headlining arenas in two years for the price of a two-drink minimum. I’ve seen genuinely famous people do surprise drop-ins at small shows. It’s one of those things that can only happen here.
Eating at a counter alone. This sounds sad if you’ve never done it. It’s not. It’s one of the most New York things you can do. Sit at the bar at a ramen shop. Sit at the counter at Joe’s Shanghai in Chinatown (9 Pell Street). Sit at the counter at any good diner. Order exactly what you want, eat it at your own pace, and watch the kitchen work. I eat alone at restaurants at least once a week and it is genuinely one of my favorite activities. New York is a city that respects the solo diner. Nobody will look at you weird. Nobody will ask where the rest of your party is. You’re just a person eating food, and that’s completely fine.
Grand Central Terminal’s ceiling. Everyone walks through Grand Central. Almost nobody looks up. The ceiling of the main concourse is painted with a mural of the zodiac constellations in gold against a teal blue sky, and it is breathtaking. Go during a quieter time (early morning or late evening), stand in the middle of the main hall, and just look up. There’s also a spot on the dining concourse level where you can stand in one corner and whisper into the wall, and someone standing in the opposite corner can hear you perfectly. It’s called the whispering gallery and it’s right outside the Oyster Bar. Free, weird, and delightful.
Washington Heights. I know I said I’d cover neighborhoods separately, and I will. But I have to mention this one here because it gets left off of almost every tourist guide. Take the 1 train to 181st Street. Walk around. Get a chopped cheese from a bodega on St. Nicholas Avenue. Walk through Fort Tryon Park (combine it with a Cloisters visit). The energy up here is completely different from Midtown or downtown, and it’s one of the most vibrant, real-feeling neighborhoods in the city. The Dominican food is outstanding. Try Malecon at Broadway and 175th for rotisserie chicken that will genuinely change your understanding of what chicken can be.
My “If You Only Have One Day” Answer
People ask me this all the time and my answer is always the same. Here’s what I’d do with a single day in New York.
Start in the morning with a bagel. A real one. I’d send you to Russ and Daughters on Houston Street (179 E Houston) for a bagel with cream cheese and lox, or to Tompkins Square Bagels (165 Avenue A) if you want something a little more neighborhood-y. Get a coffee. Walk through the East Village and soak in the energy.
Take the subway (the F train from 2nd Avenue) down to York Street in Brooklyn. Walk across the Brooklyn Bridge toward Manhattan. Take your time. Take your photos. Arrive in Lower Manhattan around midday.
Walk north through the Financial District. Pop into the Oculus at the World Trade Center, which is this wild futuristic transit hub designed by Calatrava that looks like a giant white bird taking flight. Walk a few more blocks north to Chinatown and eat something incredible for under $8. Dumpling houses on Eldridge Street. Hand-pulled noodles at Super Taste (26 Eldridge Street). Soup dumplings at Joe’s Shanghai.
After lunch, take the subway uptown to Central Park. Enter around 72nd and walk north for an hour or so. Let yourself get a little lost in the Ramble. Emerge on the east side and walk down Fifth Avenue past the Met (even if you don’t go in, the steps are worth sitting on for ten minutes).
In the evening, head to the West Village. Walk the tree-lined streets. Get dinner somewhere good. I’d say Via Carota (51 Grove Street) if you can get a table, or Emmett’s (50 MacDougal Street) for Chicago-style deep dish if you want something fun and different. After dinner, walk to the Hudson River and watch the sun go down over New Jersey. End the night with a drink at a jazz bar (Smalls Jazz Club at 183 W 10th Street, cover is usually $20 and it’s worth every penny) or a comedy show.
That’s one day. That’s a full, beautiful, real day in New York. You didn’t need to go to Times Square. You didn’t need a hop-on hop-off bus. You just needed good shoes and a willingness to walk.
And honestly? That’s what I want for everyone who visits. Not a frantic checklist. Just a day where you feel like you lived here, even if it was only for a few hours.
Come visit. Text me when you get here. I’ll probably send you this article and then meet you for pizza.