The City that Never Sleeps, the Big Apple, The City. There's no city quite like New York City (NYC). It's not for everyone, and yet, everyone should experience NYC at least once.
NYC is the muse that created Weekend Pilgrim. We wanted to help visitors make the most of their time and experience the best NYC has to offer. Sure, you can be touristy, but its so much more fun to experience NYC like a local! We’ve revised this list so many times because NYC keeps changing for better or for worse.
Regardless, we’ll save you the suspense- you can't do it all. There's about 18,700 restaurants in NYC alone! That's a different restaurant every day for the next 51 years. To tackle the beast that is NYC, Weekend Pilgrim divided the city into separate boroughs, plus Harlem! This section features Manhattan- perhaps the most famous and the center of our great city. It is filled with unique neighborhoods, plenty of culture and diversity, and a wealth of experiences that has no rival. Remember, NYC is meant for multiple trips! Enjoy and come back soon!.
Day 1: Downtown Beginnings – The Bite and the Hustle
Start your day where New York tastes most like itself—loud, unapologetic, and a little greasy around the edges.
Russ & Daughters Café, Orchard Street – A temple of smoked fish and tradition. Bagel with gaspe nova and cream cheese, or maybe a bialy and sable if you’re feeling bold. Sit at the counter, sip coffee, watch the controlled chaos of the Lower East Side hum around you. This place isn’t trying to impress you—it just is.
Soho & Prince St. Pizza – Forget the influencers and designer stores. Wander the cobblestone streets south of Houston, where the cast-iron facades whisper about the artists who lived here before the rent crushed creativity. Duck into McNally Jackson Books, stop by The Drawing Center—it’s small, brilliant, and unpretentious. Soho rewards those who move slowly. For lunch, Prince St. Pizza is the best of the City. You’ll smell it before you see it—the oil, the spice, the heat from the ovens. Their Sicilian slice with pepperoni cups is a love letter to grease and glory. Don’t eat standing like a tourist. Take it down the block, lean on a stoop, and let that first bite remind you why you live here.
Manhatta, Liberty Street – Sixty floors up, where the skyline stretches out like a promise. The food is refined but rooted—beef tartare with rye crisps, halibut with fennel. Order a martini, sit by the window, and take it in. This is what living here is for.
LES at Night – As the sun drops, the Lower East Side becomes itself—gritty, magnetic, full of contradictions. Slide into Attaboy for a cocktail you didn’t order but absolutely needed. Wander by Bowery Ballroom—someone good’s probably playing. Maybe end at 169 Bar, where the cheap beer and neon glow make everyone look like they belong.
Day 2: Uptown Grace – Quiet Confidence and the Art of Living Well
New York isn’t all chaos—it’s also refinement, subtlety, and a long lunch that stretches into something resembling peace.
Clinton St. Baking Company, LES – Get there early or prepare to wait—it’s worth it. Their pancakes are the best in the city, period. Soft, buttery, with that whisper of caramelized edge that keeps you going back for “just one more bite.” Locals know: weekday mornings are your best bet for calm.
The Metropolitan Art Museum (Met) – This is NYC's finest museum. This is NYC's version of the Louvre. It's huge. You can get lost, spend an entire day at various exhibits and do it again the following day. By the way, you can often find awesome cupcakes at a local food cart outside!
Café Boulud, Upper East Side – Daniel Boulud’s neighborhood restaurant. Elegant but not showy. Try the roasted chicken—it’s deceptively simple, and that’s the point. Service so smooth you’ll think you imagined it. You come here not to be seen, but to breathe in a city that’s mastered subtlety.
Aldo Sohm Wine Bar, Midtown – Tucked behind Le Bernardin, this is where people who actually love wine go. No pretense—just good conversation and even better pours. Sit at the communal table, talk to strangers. Order the charcuterie board; linger. The night’s young, and so are you in this light.
Day 3: Heartbeat of the City
If New York had a soundtrack, it would be the hiss of a flat top, the crack of a taco shell, the laughter spilling out of late-night bars.
Coffee and Pastry at Little Cupcake Bakeshop, Prince Street – This isn’t just sugar—it’s craftsmanship. Try the Brooklyn Blackout cake or the Chocolate Chip Banana Bread Cake with Nutella if you’ve had a rough week (and who hasn’t?). Locals slide in for espresso and small talk. It’s the kind of spot that reminds you—sometimes sweetness is rebellion in this city.
Chelsea, the High Line & Los Tacos #1 – Walk the High Line from 14th up to Hudson Yards, where art installations, wildflowers, and skyline views blend into something distinctly New York. Stop into David Zwirner Gallery or Pace—free, world-class, and refreshingly uncrowded before lunch. Then head to Chelsea Market for Los Tacos #1. The carne asada taco is religion here. Simple, honest, and perfectly balanced. Stand at the counter, lime in one hand, taco in the other. No forks, no nonsense, just flavor that slaps. If you don’t get a little messy, you did it wrong.
Greenwich Village – Take your time here. The Village is New York’s living heartbeat—bohemian but not performative, steeped in jazz, poetry, and rebellion. Stop in Sullivan St. Tea shop - yes, it’s worth it. Wander down MacDougal Street, grab an espresso from Caffe Reggio (where Ginsberg and Dylan once argued about God), peek inside Washington Square Park. Buskers, chess hustlers, NYU kids—it’s chaos that somehow feels like home.
Chinese Tuxedo, Doyers Street – Once an opium alley, now a moody, modern temple of Cantonese flavors. The roast duck noodles and prawn toast hit like poetry. The space—brick, candlelight, echoes of jazz—feels like stepping into another era. Stay for a nightcap at Peachy’s downstairs. It’s all connected.
Day 4: Making beautiful music
Manhattan teaches you one thing—survival deserves celebration. End high, eat well, and look down on it all with a grin.
Central Park – Walk uptown and lose yourself in the Ramble. The park is New York’s great equalizer—Wall Street suits and Harlem poets sharing air. Sit on a bench by the lake, maybe feed a bird or two, and let the city’s pulse fade into a low hum.
Chirp, Midtown East – Tiny spot, big heart. The kind of local joint where the eggs are always perfect, the bacon unapologetically crisp, and the staff remembers your name if you come twice. A working person’s breakfast—no avocado toast in sight.
Guantanamera – This one is a sleeper! Guantanamera offers really authentic Cuban food that rivals the best of Miami. It may be a bit noisy, but for good reason. Guantanamera also brings you amazing live music. For the perfect meal, try Azucar Mixto, Bistec de Palomilla, and Tres Leches, and a Mojito to wash it down. Dancing is welcome for the brave!
Village Vanguard – Let’s experience live music, preferrably jazz, in a close setting. We like the Village Vanguard, though Blue Note, BB Kings, and many others could easily make the list. Vanguard opened in 1935 and has hosted the legendary John Coltrane and Bill Evans.
And More…
This isn’t a checklist—it’s a rhythm. A slice, a taco, a plate of duck noodles, a drink shared too late. Here’s to being stubborn and consuming as much of NYC as you possibly can!
Times Square – Yes, this is a picture of Times Square. No, I don't really recommend it. Quite honestly, New Yorker's stay away- far away. Of course if visiting New York for the first time, Times Square is likely on your sightseeing list. To satisfy all parties, we recommend you visit Times Square....on your way to a Broadway play or musical. Don't forget our friends in "off Broadway" plays as well! Both classifications literally indicate the location of the theater but you should pick a show that best caters to your interests. Check-out www.broadway.org for ideas on cheap and last minute tickets.
Jacob’s Pickles – Weekend Pilgrim might just be Deputy of the Jacob's Pickles fan club. We've been going here for years- since the early days of the Upper West Side restaurant. And now, we can hardly get a table due to JP's growing popularity. Although Jacob's Pickles has specialty dill, it's not their best dish. Try any of the open-face Biscuit Sandwiches, Grit Crusted Fried Green Tomatoes, and the Mac & Cheese. Don't forget awesome drinks and desert to match.
Jojo – In our humble opinion, Jean-Georges' first restaurant is also his best. Jojo, a French bistro situated within a cozy, yet elegant townhouse is a classic and absolute gem within a sea of New York City restaurants. Basically, we like it...a lot. Go here for a fancy evening on the town or for an upscale lunch. To match the beautiful décor, JoJo offers excellent seasonal prefix or a la carte menu options!
Katz’s Deli – Harry met Sally in Katz's Deli. And if you saw the movie, you'll know that Sally really enjoyed herself. Who can resist pastrami piled high? The lines are long, but you're greeted with deli samples while you wait. Each order is huge so doggy bags are welcome!
Magnolia’s – Cake, cake, cake! Please save room for desert. Words won't do Magnolia Bakery justice. You have to see it for yourself. The smell of fresh cupcakes will greet you down the block before you step food in the door. We recommend red velvet or caramel cupcakes with caramel meringue buttercream (pictured). You can always try a "Daily Cupcake" which features a different selection on each day of the week.
Guggenheim – You can find art and culture throughout the City. It's in your face in the graffiti of the Lower East Side. It's on the sidewalks, sold by street vendors. It's people-watching in the park and it's within the many museums and galleries across the City. One of our favorite art galleries is the Guggenheim. This beautiful building is filled with impeccable art, decorated throughout a spiral interior. There's many museums to choose from, but the Guggenheim is a gem.
Uncle Jack’s – Black tie wait staff, white napkin properly draped over arm, mahogany interior. Add steaks cooked to perfection and the impressive Seafood Tower. There are may choices for steak in NYC, but Uncle Jack's is our underdog favorite. Welcome to Uncle Jack's.
Old Time Bar – It’s a good old time. Yes, it’s in the title. Plus, hey, our favorite bartender and family friend works here!
