It was hard to admit that it took me this long to get to New York City in the first place. I got enough “what?! You’ve NEVER been to NYC?!” outcries in casual conversations that I decided it was high time to fly coast to coast and finally explore the iconic city.

But the biggest question was: what to do? In a city so historic, so cosmopolitan, so full of diversity, how could I distill its essence in only four days?

The truth is, you can’t. NYC is simply too much for just one visit, and I will definitely be back for more. Like so, so many others before me, New York will leave you hopelessly in love, starry eyed, and craving more.

Nonetheless, I managed to cover a lot of ground in four short days, with an itinerary centered on neighborhood exploration, food, history, and a whole lot of plain walking around without a particular destination in mind.

And it was perfect. New York in the fall is particularly wonderful; in early September the season just begins to change, with days alternating between still warm and humid days of summer and milder, breezy fall days with cool nights.

What to Do in New York City in Four Days

Day One | Midtown + the Theater District

I based myself at a great Airbnb on the Upper East Side as I have local friends there who I planned to meet up with, but it turned out that I not only found a very reasonable studio apartment rental but also had no problem hopping around the city with ease.

First up on my four-day itinerary was a low-key day of wandering, with a loose idea of a couple of destinations in Midtown, followed by a night at the theater.

Explore the New York Public Library

Without waxing too poetic, a visit to the New York Public Library was peering into the juxtaposition of old and new New York. A commanding, sturdy, and architecturally compelling building, it, to me, represents the enduring nature of the city, its longstanding history, its very foundation of access, free thought, and new ideas.

I grabbed a latte and wandered the stunning marbled staircases, long halls flanked in bold columns, adjacent academic study rooms, and its main reading rooms with incredibly intricate ceiling designs. I poked into random study rooms, perused map collections, and snapped photos of the gorgeous design at every turn.

Maybe it’s my fondness for history, beautiful spaces, and academic thought, but I found it to be peaceful and inspiring, and the perfect way to begin a slow-paced day and ease into my first NYC evening.

If I had done more planning, I would’ve checked out the library’s Visitor’s Guide and taken advantage of the audio tour or the visitor film. Yet, sometimes spontaneously exploring on your own is enough, and it was.


People Watch at Bryant Park

I’m an avid fan of city parks, and found Bryant Park to be busy and thriving in a good way. People sat at many an iron cafe table with a coffee, a book, or a friend; sat in groups on the lawn with a picnic; even hoola hooped or practiced acro-yoga together – but it felt like a joyous, beating heart in the middle of the concrete jungle.

Like Jane Jacobs, urban scholar and activist heralded as the defining voice of community-centered, place-based city planning, I love cities, and am fascinated by their pulse, their ecosystems, and the way they both shape the individuals living within them, and are shaped by those people. Read The Life and Death of Great American Cities, it’s fascinating.

“…that the sight of people attracts still other people, is something that city planners and city architectural designers seem to find incomprehensible. They operate on the premise that city people seek the sight of emptiness, obvious order and quiet. Nothing could be less true. The presences of great numbers of people gathered together in cities should not only be frankly accepted as a physical fact – they should also be enjoyed as an asset and their presence celebrated.”
Jane Jacobs

Seeking out free public space is of course a budget-friendly tactic for any seasoned traveler, but also an exceptional way to interact and observe locals. In New York, think beyond Central Park (though more on that later) and explore smaller parks and community spaces – you’ll discover the unexpected there.

Eat at Kati Roll

New York is known as a mecca for food culture, along with being the hardest place to get a dinner reservation in the nation, but my foodie-ness has its limits and I’m an ardent supporter of street food and hole-in-the-wall eateries. Sometimes, you gotta find a cheap bite and a cold beer, but do so in a way that would make Anthony Bourdain proud. Thanks to handy old Yelp, I stumbled upon The Kati Roll Company, a family-owned eatery with five locations in Manhattan and one in London specializing in Indian street food.

A taste of Kolkata, a kati roll is a scrumptious wrap of spiced grilled meats and various toppings swaddled in buttery parantha bread or roti. I grabbed a shami kabab roll with minced lamb and lentils and a beer, and observed as the clearly local crowd rolled in on their way home from work or gathered in groups for after work social hours. The food was incredible, and the small space with low lighting, small wood tables, and brick walls graffitied with old Bollywood movie posters and layered paints evoked the warm streets of Kolkata. My only regret is not ordering two rolls.

Go to a Broadway Show

Taking yourself to the theater solo is delightful. After a meal out at an Italian restaurant on the Upper East Side, I put on a classic black dress and heels, hopped in a lyft, and admired the city lights as we whisked down Park Ave on my way to see The Lion King at Minskoff Theater – a long-running show I’ve always wanted to experience first hand.

Glittery Times Square is almost tolerable at night, when the energy of a bustling night out is stimulating, and the lit up marquees scream New York glitz and glamour.

I was, however, apparently overdressed for what I thought was a more decadent and tasteful affair – I was disappointed to be surrounded by tourists in jeans and t-shirts, and joked with the lovely attendant at concession as she poured my wine into a plastic branded sippy cup. “Oh no girl, it’s all tourists and plastic cups here. Want a double?” Sigh. Why not.

Despite that minor realization, I still rocked my dress and my wine sippy cup and had a great seat stage right. I sat between a posh couple from Israel on holiday and a family group with the recognizable accents of South Carolina, and I chatted nicely with both before the lights went down and the curtains rose.

Director Julie Taymor, who’s early career in Southeast Asia was steeped in the music, movement, and traditional masks of the region, expertly and passionately weaves the familiar children’s story into a beautiful, colorful, moving stage production. I literally cried in the opening rendition of “the Circle of Life,” as the actors moved down the aisles in awe-inspiring elephant, bird, and giraffe costumes made of wood exoskeletons, bright fabrics, and intricate masks. The cast was amazing, the costumes continued to inspire, and the music tugged at all the right emotions.

Do yourself a favor and see this show. Even dress up if you like – it’s the New York City theater for fucks sake!

New York will leave you hopelessly in love, starry eyed, and craving more.


Day Two | Central Park and the MET

After parks, historic buildings, and a night at the theater, I continued my cultural tour of the city with an essential exploration of New York’s 843 acre urban sanctuary between Fifth Ave. and Central Park West, and a visit to the dreamiest art museum of them all.

Walk Around Central Park

At the very heart of Manhattan lies a huge green oasis, a place that defines New York as much as the towering buildings that surround it. Comprised of open fields, wooded areas, walking paths, bridges, lakes, and various public attractions from an ice-skating rink, restaurants, concert venue, and zoo, it seems an outdoor respite for urban New Yorkers and tourists alike.

I packed a picnic of fresh bread, marinated olives, hard salami, and cantaloupe from the health food store near my airbnb and took a walk with absolutely no map or destination in mind. I ended up next to one of the many notable stone bridges, under which a busker passionately pounded out Beethoven on a keyboard. I tossed $5 in his case and sat contently on the concrete steps for my own personal concert – it was a special and lovely moment of serendipity.

Serendipity: finding something when looking for something else, thanks to an observant mind

I was pleasantly surprised by how wild Central Park actually feels. There’s enough space that even with the loads of people, you can find yourself walking alone or settling into a peaceful personal spot. It’s also surprisingly quiet, with the trees blocking out the city noise shockingly well.

We’ve already established my love of public space, and Central Park really lives up to is fame. After walking, observing, snapping photos, and picnicking for a couple hours, feeling content and refreshed, I followed a path north to explore the MET, which is neatly tucked in the park off Fifth ave.


Spend Hours at the Metropolitan Museum of Art

Oh, the MET – how I love thee. One my absolute favorite things to do on a solo trip is visit art museums – it gives you time to gain quiet inspiration, be alone with your thoughts, and explore at your own pace. I’ve been dying to visit the MET since I was a youngin’, holding it as the highest bar by which every other museum would be compared.

I’m a huge fan of impressionism and post-impressionism, and nearly cried (literally) when I turned a corner and peeped my first Van Gogh in person. I don’t care if you think Van Gogh is “played out” or you think any Van Gogh lover isn’t a “real” art aficionado – there’s no one who captures as much fluid movement and intense emotion in a thick brush stroke as Van Gogh. I was equally enamored with every Degas, Monet, Seurat, and Cezanne I stood before. I reveled in the originals of my second favorite, the legendary Toulouse-Lautrec, starry-eyed at every intimate and romantic nude, wispy dancer, and steamy Moulin Rouge depiction. (Side note: I found later that the MET website describes Toulouse-Lautrec as an “aristocratic, alcoholic dwarf known for his louche lifestyle,” which is a bit harsh, no? Just because one dies of syphilis and favors seedy dance halls and the downtrodden doesn’t mean their contribution to art should be viewed in any different light. Amirite?)

Beyond 19th century European art, the MET is home to a simply fantastic collection of art from Oceania, sub-Saharan Africa, and the early Americas. I was inspired by the intricate masks and ceremonial objects of Africa and Indonesia, and mesmerized by the towering wooden totem figures of Papua New Guinea. A must see: the huge installation of an intricately painted ceiling from an ancient ceremonial building from Papua New Guinea – absolutely stunning.

I could tell you more about my favorites, from the ancient Egyptian collection to the modern and contemporary art wing, but you’ll simply have to explore for yourself. I spent four hours discovering everything from Jackson Pollock and Georgia O’Keefe to ancient Greek and Roman art, and another half hour in the gift shop searching for the perfect large scale Rothko print.


Day Three | Lower East Side + Red Hook, Brooklyn

I was basically in a state of perpetual happiness by day three, so inspired and in love with NYC. I couldn’t get enough. Now, I ventured to the eclectic lower corner of Manhattan and across the East River to artsy Brooklyn in search of the spirited character of each neighborhood.

Visit the Tenement Museum

People have plenty of preconceived notions of New York City, probably mostly informed by pop culture, but also hopefully by some history books. Whether the big city of opportunity for many a young dreamer to the seedy underbelly of a crime noir novel to the penthouse playground of the wealthy elite and celebrity along Park Ave West, one narrative we all know so well is the city of promise and port of hope for multitudes of immigrants, then and now.

It may not be on everyone’s list of sights to see in New York, but for a former student of social justice, politics, and feminism, New York’s lower east side is steeped in culturally and socially significant history.

It’s silly, but when I was younger I was so incredibly impacted by a young adult historical fiction novel I read about the life of a young Russian Jewish immigrant girl that it’s stuck with me into my 30’s. Her story centers on her struggle with keeping old traditions in the new world and living in a tiny tenement; her sister’s advocacy work in the pre-union era of garment sweatshops; and her best friend’s death in the tragic Triangle Shirtwaist Factory Fire (another significant event I obsessed over in my formative years leading to my university studies and feminist awakening).

(Side note: If you have a daughter, niece, etc. buy her the Dear America series, specifically Dreams in the Golden Country. Seriously, every little girl needs it.)

Anyway, the Tenement Museum is worth a visit if you’re at all interested to learn and see the very beginnings of New York’s Lower East Side at a time when immigrants helped to craft the very fabric of the city and our nation. The museum offers guided themed building tours, neighborhood walking tours, and a great little gift shop that supports their efforts (where I scored my now-favorite I heart NYC coffee mug. If ya gotta buy it, why not here rather than at the airport?).


Eat at an Iconic NYC Jewish Deli

As an insatiable consumer of travel and food magazines and blogs, I would be remiss if I hadn’t heard of Russ and Daughters. Making every list of “Best Places to Eat in New York” by any list that matters and donned “the essence of New York City” by celebrated French chef Alain Ducasse, Russ and Daughters is a New York institution. Opened in 1914, the counter-service Jewish “appetizing” store is celebrated for its smoked fish of every kind, caviar, cream cheese, bagels, pickled salads, and a multitude of any other Jewish comfort food from matzo-ball soup to house-made challah.

I originally made my way down to the Lower East Side on Rosh Hashanah, unknowingly obviously, as the store is closed on Jewish high holidays. I was near devastated, but just decided to spend two days in the neighborhood – all in the name of pickled fish.

I stuck to what I like – an everything bagel with Norwegian smoked salmon, chive cream cheese, capers and onions – which I stood in the crowded counter-style shop for for a good hour, but it was worth the wait. The sense of community felt especially strong the day after the holiday as “Happy New Years” were exchanged across the counter. The old-timey feel of the glass counters packed with curated products, the expert hands of the counter workers carefully filleting and spreading, the friendly conversations of patron and merchant was everything I expected a New York food and cultural institution to be. It’s no wonder four generations of the Russ family have managed to keep the tastes and traditions of New York alive in a tiny hole in the wall in lower Manhattan.

Next time, I’m going for the trout roe and pickled herring.

Russ and Daughters now also operates a cafe around the corner on Orchard St. that I’d recommend if you’re not as committed to visiting the original storefront.

See the Statue of Liberty From the Water

I had wanted to see the Statue of Liberty, that iconic character embodying so, so much (that’s a discussion far beyond this simple post), but not necessarily by staring at her feet after shelling out an admission fee. I was on a short timeline, after all.

So, I researched a lot, and found three insider ways to see our lady beacon of hope from the water: 1) from the Staten Island Ferry, 2) from the Governor’s Island Ferry, or 3) via the Red Hook Ikea water taxi. I opted for route number three, which is normally only $5 but free on the weekends, as a way to hit two birds with one stone – a statue viewing and a quick way to get to Brooklyn. Huzzah!

Admittedly, the water taxi doesn’t get too close to our Lady of Liberty, but I managed to see her, still inciting a bit of excitement in my chest, and was able to snap a few grainy, distant photos. But ever the optimist, I also enjoyed the Manhattan skyline views, experiencing the smell and feel of the East River harbors, seeing the expansive bridges from a unique vantage point, and just being on the water, with its dark, cold Atlantic waters and seagull cries. All among the locals on their way to purchase a new rug and lamp, rather than a selfie-stick toting tourist – so, high five!



Eat Seafood in Brooklyn

The bartender at Brooklyn Crab in Red Hook was impressed with my water taxi savviness and applauded me as he slid a Mermaid Pilsner from Coney Island Brewing Company across the bar. The busboy, on the other hand, couldn’t comprehend why I was eating alone. “You’re here by yourself? ….Why?!”

Dining alone can be boring and even anxiety-inducing as others stare and wonder why you’re solo, but if you approach it from a different light, you might just be surprised by what you’ll notice and take in – things you otherwise might’ve missed in the distraction of company.

I noted the way the sun struck the clouds and rooftops in such a dreamy way after the brief rainstorm I luckily missed, and how the host and waiter played out a spirited flirtation on what I imagine was a routine late afternoon shift. The seafood was of that crisp, cold ocean variety, and entirely satisfying.

Trying to conserve my dying iphone battery, I occasionally chatted with the waiter over my bowl of clam chowder, plate of blue crab cakes, and chilled pilsner – how the place fared in the winter, when the now-wide-open shutters overlooking the harbor were clamped shut to keep out the coastal winter chill; what the best local beers were, and where else to go in Brooklyn.



Walk Across the Brooklyn Bridge

Despite being armed with local recommendations, the day waned and I didn’t get the chance to see much of Brooklyn beyond that small corner of Red Hook, but with the afterglow of a great meal and a couple drinks, I happily made my way to the entrance to the Brooklyn Bridge, aiming to walk across right at sunset for the best view.

The air chilled considerably, the wind forcefully slapped me in the face the whole time, and I nearly lost my wind-took sunglasses to the traffic below, but I managed to make it to the middle of the infamous bridge right as the sun lowered in the sky and set the Manhattan skyline to a soft pink and purple backdrop.

I love that moment when it starts to get dark in a city and the buildings light up and the energy becomes electric. It’s more apparent in the fall and winter, when the air is thin and the city’s intensity becomes intoxicating. I don’t care how cheesy that sounds; that’s the magic of cities.

Day Four | Chelsea + the Meatpacking District

Stroll the High Line

Complete honesty? I could’ve done without a trip to the High Line. It seriously underwhelmed me. Perhaps because it was so packed that strolling was more like shuffling along in a single file line, or because I was constantly comparing it to Chicago’s 606 which is wider, greener, and just all around better. Or because I was asked multiple times to take other tourists’ photos when just trying to sit on a bench and eat a bagel (but points for blending in and being mistaken for a local??). The views aren’t really that great because you really are only elevated two stories.

The good thing about making my way there, though, was pinpointing stops for my next visit. I was intrigued by The Highline Hotel, the Market NYC in SoHo (spotted en route to the High Line in the cab), and any one of the adorable cafes and restaurants along 10th ave.

“…That moment when it starts to get dark and the buildings light up and the energy becomes electric…That’s the magic of cities.”

Tips for Traveling to NYC

A few quick opinions from my trip you can take or leave:

Take the Subway

You haven’t experienced a city until you’ve ventured within its belly, found its pulse, and coursed its veins alongside everyday commuters. Though a Chicago city girl at heart, the subway isn’t as intimidating as tourists often believe, and not taking advantage of cheap and easy public transit in an urban center is a huge disservice to yourself and the city. Even if, like me, you first jump on a train going in the opposite direction or witness near physical brawls on your way to the next attraction, just be aware of your surroundings, hold your bag consciously, and consider yourself lucky for being part of something real.

Cab It From the Airport

Are there cheaper ways to get from the airport to anywhere in the city? Yes. Is there a public transportation route you can take? Yes. But, personally, after getting off a six hour flight, I just want to jump in a cab and let someone take me to where I need to go. Even traveling light with only a carry on, the thought of lugging around a bag on the subway and/or bus when all I want is a shower and a post-flight cocktail is awful. So, the $70 cab or $50 lyft/uber is, in my opinion, well worth the ability to sit back and take in your new destination a bit before gathering yourself and setting off to the first bullet point on your itinerary. I’m not the ultimate budget traveler, though no criticism of those maximizing their spend; I’m an experience-seeker who knows when she needs a nap or a quiet hotel room to recoup so that the next outing is more enjoyable and I’m able to be fully present and active.

Avoid Times Square

Beyond seeing a show, just don’t do it. Unless you’re somehow inspired by thousands of tourists taking selfies, a gross, seizure-inducing display of capitalism in the form of blinding billboards, and the literal inability to enter or leave the area by cab due to insane traffic, then go for it. Is that cheap H&M outfit going to be better because you bought it in the enormous Times Square store? No. It was still made in the same factory in Phnom Penh, even if it’s super cute. See the New Years Eve ball drop in Times Square on tv from the comfort of your living room, it’s really not worth wasting time on.

Carry a Phone Charger Wherever You Go

Navigating via smart phone when you’re not worrying about data usage is the modern traveler’s forte. But, a dead iphone is not only a missed photo, but the tenuous lifeblood between being stranded and on schedule. Thankfully, every lyft driver I asked was more than happy to let me charge my phone; or I managed to find an outlet under a bench at the MET or at a seat at the bar. This strategy literally saved me on this trip.

Local recs for my next trip? Leave them in the comments!

Photography note: not all of these photos are mine, though many are. The others are carefully curated from the talented photographers partnering with Unsplash in order to help capture the emotions of this trip where I failed to do so.