There is a reason New York City is called the city that never sleeps. When I visited with my friend in the summer of 2016, we spent three days doing as much as possible, but I know that we didn’t even scratch the surface.
That being said, I had an absolutely amazing time hitting some highlights around the city. In this guide, we’ll take a look at how to spend three days in New York City, including some tips to help your trip go smoothly.
Day 1: Times Square and New York Comedy Club
The plane touched down at JFK airport in the morning and the most cost-effective way to get into the city was on the Plane Train. Two transfers and an hour and a half later, we emerged from the subway into the New York City sunshine.
We dropped our bags at the Jazz on the Park Hostel (located right next to Central Park, much to our delight!) and spent some time getting oriented with our neighborhood. After admiring the park and the intricate brownstone homes that seemed to go on for miles, we jumped back on the subway to head to Times Square.
Visiting Times Square
Of course, when we first saw Times Square we stood in the middle of the whole thing staring up in awe. I was posing for a picture when a charismatic man selling tickets to a comedy show that night approached.
Normally, I would be skeptical of buying tickets for a show from a stranger, but we spent some time chatting, haggled, played it cool, haggled some more, and walked away with two tickets to the comedy show later that night. We also got a list of the best restaurants and attractions in the city, handwritten on a scratch piece of paper by our new best friend.
He also let slip another tip that would become a game-changer. Apparently, the theaters give out a few dozen Broadway show tickets every morning at deeply discounted rates. He recommended we get to the theater 30 minutes before the theater opens and keep our fingers crossed. We set our morning alarms accordingly.
Relaxing in Bryant Park
Eager for a bit of quiet after the bustle of Times Square, we wandered up the street toward Bryant Park. After the travel day frenzy, putting our feet up and relaxing was perfect.
We knew we couldn’t stay in Bryant Park forever, so after feet were sufficiently rested, we ventured south right past the Empire State Building and the Flatiron Building, one of the world’s first and most iconic skyscrapers.
New York Comedy Club
After stopping for dinner at a restaurant recommended by the ticket salesman, it was time to walk to the New York Comedy Club.
The Emcee for the night was the fantastic Pat Brown, who had just released her album that day! She introduced about a half dozen other comedians and kept us laughing the whole time. The crowd was small, the comedians were very personal and though the show was a comedy, there were moments of very real discussion and openness. An excellent experience all around.
230 Fifth Rooftop Bar
After the show, we made our way to the 230 Fifth Rooftop Patio bar. The elevator doors opened and suddenly we were surrounded by the city. The indoor and patio space had floor-to-ceiling windows overlooking the city and impeccable views.
Even though we didn’t go up in the empire state building, this view made it look close enough to touch. I spend the night ogling over the beautiful NYC skyline. I felt like I had seen so much already on day one, and I was ecstatic for what the next few days would bring.
Day 2: Central Park, The Met, and Broadway
My second day in NYC began with a clear mission. We knew that theaters gave out discounted Broadway tickets (called Rush Tickets) to the first few dozen people in line at the theater when the theater opens, and we were determined to get some.
Broadway Rush Tickets
As we careened through the maze of subway tunnels heading toward the theater district, we discussed which shows we most wanted to see. We landed on Les Misérables because it is a classic and we knew it would make all our musical theater-loving friends jealous.
When we found the theater, the line wrapped around the block. At 10:00 am, the Imperial Theater doors opened and the line slowly started to move forward. Group after joyous group of people in front of us emerged with those sacred tickets as we anxiously counted the heads in front of us, hoping somehow we would get a lucky ticket.
When it was finally our turn at the ticket counter, the man said, “I’m sorry, we are all out of rush tickets.” We were crushed, but then he continued “But I do have some discounted tickets in the Balcony, are you interested?” Winner!! We would be seeing a timeless Broadway show that night and we couldn’t be more thrilled.
Exploring Central Park
After the exhilaration of the morning, we decided the rest of the day would be devoted to relaxing in Central Park. We ate lunch at the cafe outside the Loeb Boathouse and enjoyed heaping portions of fries and equally beautiful lakefront views.
Lunch beside the lake inspired a trip out onto the lake in a rowboat. I learned a very important life lesson out there: I’m not very good at operating a rowboat. Luckily our boat was creaky, which alerted other boats before I had the chance to accidentally crash into them.
Looking for more things to see in Central Park? Make sure to check out Six Stops to Make in Central Park by Sarah over at Suitcase Six!
The Metropolitan Museum of Art
Arms sufficiently tired, it was time to tackle the Met. My infatuation with the Met began when I was in middle school and I read the book, From the Mixed-Up Files of Mrs. Basil E. Frankweiler.
In the story, two kids run away from home and live in the Met. It was my first “Favorite Book” that I read many times, and I have to say that the Met lived up to all my expectations.
The hardest thing about visiting the Met is leaving the Met. There were rooms full of medieval armor, turn another corner and we were transported to ancient Egypt. Some rooms had furniture, others paintings, others sculptures, and every space was more fascinating than the next. It’s a place I could easily see myself spending days and days.
Les Mis on Broadway
Like the Met, Les Mis was everything I expected and more. My seat was in the actual last row of the theater and it was still amazing. My desire to become a Broadway star? Absolutely reawakened.
Day 3: Black Tap Milkshakes, Battery Park, and Lombardi’s Pizza
Day three in NYC began at Black Tap, a burger and milkshake restaurant in SoHo. We had high hopes of scoring one of those magical-looking milkshakes that are all over Pinterest and Instagram. If you haven’t seen them, they are enormous with entire slices of cake or cookies or full-sized candy bars stuck to the side. Quite preposterous, so of course we had to get one.
We arrived at Black Tap, optimistic and naïve, and walked right up to the door. As I boldly pushed through the door of the burger joint, I heard a voice behind us utter those crippling words: “The line starts back there.” In a wave of milkshake excitement, I completely missed the line, marked off by a thin rope, that ran the length of the block.
The wait was over two hours long so we gave up our milkshake dreams and decided to eat lunch at a nearby Mediterranean place before hopping on a subway to lower Manhattan.
Lower Manhattan
We walked down Wall Street and then passed the NY Stock Exchange. After taking an obligatory picture with the Charging Bull, exploring Battery Park was a breath of fresh air.
When I’m walking through the tangles of the city, I always forget that New York is surrounded by water. So it was quite exciting to emerge from the financial district and see soft rolling waves and then, right there out in the middle of the water, the Statue of Liberty.
High Line Park
Eager to cross more off our “NYC To Do List,” we ventured back up toward Chelsea to the High Line Park. This park, according to my friend, used to be a decommissioned train track that had fallen into disrepair.
Rather than tear it down, someone had the wonderful idea to turn it into a long, narrow, train track-sized park! Swarms of people were out walking the High Line, which runs about a mile. Art installation pieces and parts of the old train track are intermingled with flowers and shrubs, creating a skinny, linear oasis high above the busy streets.
At the end of the High Line, I sat down on a bench to rest my very tired feet. I pulled out my phone on a whim and was delighted to learn two things. First, there was another Black Tap Milkshake location in the Meatpacking district. Second, we were currently in the Meatpacking district!
Black Tap 2.0
It was just a few blocks away so we walked up and there was no line! We walked right in and sat down immediately. Our milkshakes were incredible.
We split the salty and sweet one – a peanut butter milkshake served in a glass with M&Ms and Peanut Butter Cups frosted to the side, chocolate dipped pretzels, chocolate fudge, sugar daddy candies, pretzel sticks, and a million other things I’m sure.
Lombardi’s Pizza
Hyper with sugar, we followed our noses to Lombardi’s for dinner. The founder, Gennaro Lombardi, is credited with creating New York Style Pizza and opening the first pizzeria in the United States. If you’re a pizza fan, this is definitely a place to check out.
Wanting to make the most of our last night in NYC we took a stroll toward the water and one of the most beautiful spots in New York City found us when we least expected it.
6 Tips for Visiting New York
I’m constantly in awe of how much there is to see, do, and eat in New York City. Visiting this city is definitely an adventure, so in this section, we’ll look at some Tips for Visiting New York City if it’s your first time.
Download CityMapper or the NYC Subway App
I’ve never been good at reading subway maps. Normal maps? Sure, no problem. But subway maps get me all tangled up. The City Mapper app let me put in a start point and an endpoint, then gave nearby subway stops and the trains to take. I probably would have ended up in Canada without it.
Get up early for Broadway Rush Tickets
If you’re visiting New York on a budget, it’s worth the (not so early) morning wake-up to get such a good deal on Broadway tickets.
Figure out what theater your show of choice is playing at, get there 30-45 minutes before the theater opens, wait in the line at will call, and bring a snack. It will be a long morning but it was worth it.
Go to Black Tap in the Meatpacking District
It is hard to pass up those delicious milkshakes. The Meatpacking location has the same amazing milkshakes without the long wait. Just avoid main meal times. I went around three and walked right in and got seated immediately.
You will probably need two days for the Met
Cliche as it sounds, there was something for everyone at the Met. I saw ancient Egyptian art, a fashion exhibition, renaissance paintings, and full suits of armor. And that was only a handful of the galleries. It is quite an undertaking and definitely merits multiple visits.
The American Museum of Natural History has a less crowded second entrance
On our last day in New York, we planned to see the American Museum of Natural History. But approaching the museum with just hours left in New York City, we realized that would be impossible. The line for the museum went all the way down the block and around the corner. Hundreds of tourists and school groups waiting and no one moving.
I walked around the building because there were some amazing food stands luring me in with their aromas, and I noticed another entrance on the Columbus Street side of the museum.
The line was still too long to wait in on a tight time schedule, but it was significantly shorter than the line out front and it was indoors (and air-conditioned!) If I had the time, using the Columbus Street entrance would have been the right move.
Spend time in the NYC Parks
Spending time in the green space around the city was one of my favorite parts of the trip. Whether it is sprawling and iconic parks like Central Park, quirky and modern parks like the High Line, or this tiny hidden philosophical park I found on accident, the parks add life to the concrete.
I cannot wait for my next trip to New York City! What tips do you have for people traveling to NYC?
My first and only tip – travel with Nicola! She makes it entertaining and still hits the high lights. She does Eats and Treats well – and manages to be happy the whole time.
I echo Anne’s sentiments. Nicola must be quite fun to travel with. She would be a great tour guide! What a post!
I would vote for Nicol to be my tour guide too!! And I love the sign post from First Steet Green Art Park–how cool is that!?!