36 Hours in NYC with a Local

If you’ve already visited iconic New York City – Times Square, Lady Liberty, the Empire State Building – or you just want to experience a city through a less touristy lens, come along on my whirlwind, 36-hour guide through the city’s most happening neighborhoods. We’re covering a lot of ground, so pack a good pair of walking shoes.

One of my best friends is a fashion marketer living in Brooklyn, and last June I booked a cheap flight courtesy of Hopper to celebrate her birthday over the weekend. I loved getting an insider’s perspective on one of the most famous cities in the world, so I’ve provided a breakdown of our itinerary, in case you want to replicate our local’s day off in the city.

8:30 PM Friday Evening // Land at JFK

My flight got in at 8:30 Friday night, and left for home 8:30 Sunday morning, giving me exactly 36 hours to take in a slice of life in the city that never sleeps. So naturally, the first thing I did after arriving by Uber at her Williamsburg brownstone was hit the hay. After a stressful day of work and a frantic, rain-soaked dash to the airport, I needed my rest to be ready for Saturday in New York. But if you’re feeling up to it, I highly recommend going for a garden nightcap at nearby Huckleberry Bar or a classy cocktail the more upscale Hotel Delmano.

8 AM Saturday Morning // Coffee

Take the train to Union Square and walk through the Saturday morning farmers’ market on your way to get your caffeine fix at The City Bakery, a beautiful and spacious cafe offering a full lunch menu and renowned hot chocolate. We didn’t grab food, but I would suggest you take advantage of the delicious pastry offerings or avocado toasts on display in the coffee line. It’s going to be a long morning.

After grabbing your joe, head north up 5th Avenue and do some window shopping on your way to get a picture with the Flatiron Building. Keep going north until you see the New York Public Library. You can take a picture with the famous stone lions, but the real treat is Bryant Park just behind the library. One of my all-time favorite parks, Bryant never feels crowded, and even in the summer you can find a cool green chair in a shady spot to take a moment for lunch or an intimate conversation.

10 AM // Central Park

Keep on walking! Aren’t you glad you grabbed breakfast now? Head up 5th Ave to Central Park, and take a shady stroll through the park on your way to the Met. I think I counted three birthday parties in the small section of the park we crossed through. How many can you find?

11 AM // Metropolitan Museum of Art

Metropolitan Museum of Art NYC

When visiting the Met, I would strongly suggest picking a main exhibit to focus on, because it’s incredibly easy to get lost in all the art. We went with the goal of seeing the Heavenly Bodies fashion exhibit, which was incredible and inspiring, but we weren’t able to stop ourselves there. After drooling over damask-paneled walls, ogling medieval chainmail, and sighing over Impressionist paintings, our protesting stomachs finally got the better of us.

2 PM // Brunch

Cut across Central Park and through several blocks of adorable Upper West Side townhomes to reach a sunny transplant of southern France – Cafe du Soleil. Even though I was so hungry that I’d have eaten just about anything, I could tell my eggs benedict were perfect, and my Mimosa Soleil – champagne, orange juice, and Aperol – quickly became my new favorite brunch drink.

4 PM // Window Shopping

NYC street with pedestrians and cabs

Now that you’ve refueled a bit, it’s time for some shopping. I had always wanted to see New York’s Le Labo store, which looks a bit like the best-smelling Victorian chemist’s lab you’ve ever seen. From there, you’re perfectly positioned to browse Madison Avenue’s most illustrious tenants – Chanel, Longchamp, Hermès, Jimmy Choo, Alexander McQueen, Alice + Olivia – and act as if you have money to buy out the store. I did get a bit of a kick when a Chanel saleswoman complimented my PVC lemon slice purse, à la Cracker Barrel!

6 PM // Nap

By this time, even my friend’s NYC-accustomed feet were tired, so we walked back to the L line by way of Greenwich Village, took the subway back to Brooklyn, picked up some banana popsicles and fresh mango from a bodega, and took a power nap.

8 PM // Oysters and Absinthe

person serving oysters

Feeling refreshed? After a quick change and another coat of mascara, catch an Uber to Maison Premiere, for absinthe cocktails and some of the best oysters I’ve ever had. The website highly encourages reservations, but we were immediately seated without one. The restaurant feels cozy and inviting with an old-world sensibility. Don’t miss the fairy-filled garden in the back.

10 PM // Tiki Cocktails that Pack a Punch

Now for something more hip. Take the train into the heart of Soho and track down the atmospheric Freehand Hotel. There will be a line. When you get to the front, an usher will take you through what seems like a service hallway and up an elevator to the rooftop Broken Shaker bar. It feels like you’ve walked into an upscale tiki bar in the South Pacific, barring the magnificent view of the Chrysler Building. The drinks are delicious and strong; I recommend either the caipirinha, or their take on a Negroni, depending on your liquor of choice.

1 AM // McD’s

It’s late. After a good time with good friends and good drinks, you’re probably ready for some munchies. You could try and track down a ramen joint, or you could join me in succumbing to the golden arches of McDonald’s. The best part? Most of them now have those automated ordering screens, so you never have to talk to a person. My late-night munchies of choice? Fries and a chocolate milkshake. Divine.

6:30 AM // Leave for the Airport

JFK Airport

Give yourself plenty of time to get to the airport in the morning. I decided to be brave and navigate the subway by myself, which might have been the fastest option if the AirTrain was running. Instead, I had to take the temporary shuttle, which put me behind schedule in arriving to my terminal. Thankfully, the security team at JFK is extremely organized and efficient, and I managed to get to my gate with time to spare.

It’s possible to spend months in a city like New York and still not see everything it has to offer. If you have just one weekend, I prefer getting a feel for the pace and flavor of a city, rather than wasting precious hours standing in line for a major tourist attraction. So the next time you find a cheap flight to New York, why not go for it!

What are your favorite lesser-known spots in New York? Let me know in the comments!

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