My New York City travel story started in January 2019. Eight degrees. A Jesse McCartney concert. And my first-ever trip to New York City.
Looking back, I’m not sure what was colder…the weather or my determination to never visit New York in winter again. LOL
I had never been to New York before, so luckily, I had the perfect tour guide: one of my friends from Atlanta who had moved there. This is the same friend I visited in San Francisco and traveled with during my cross-country road trip. She showed me around, introduced me to some of her favorite places, and made sure I got the full first-time-in-New-York experience.
That first trip ended up being the beginning of a pretty long relationship with New York City. My friend moved back to Atlanta for a while, then moved to New York again, which gave me a reason to visit a few more times.
Four trips later, I’ve experienced New York in very different ways: from freezing January temperatures and Broadway shows to summer beach days, sunset views, incredible food, and being caught in a sea of people during the 2026 World Cup.
And somehow, despite my complaints about the prices, the crowds, and those confusing numbered streets, I keep coming back.
My First Trip to New York Was 8 Degrees
My first New York City trip was in January 2019, and the main reason I went was a Jesse McCartney concert. Yes, Jesse McCartney. Don’t judge me! If you know, you know.
The problem? It was eight degrees. I don’t do well with cold weather under normal circumstances, so being in New York in January was definitely an experience. I remember being bundled up and trying my best to enjoy myself while also wondering why I had voluntarily traveled somewhere this cold.
I made a promise to myself that I would never return to New York in the winter and so far, I’ve kept my word. LOL
Since it was my first visit, my friend took on the role of official New York tour guide. We spent most of our time exploring Brooklyn and Manhattan and checked off plenty of the classic New York sights. We visited Central Park, Times Square, Macy’s, the Metropolitan Museum of Art, Chinatown, and the Brooklyn Bridge.
We were also huge Gossip Girl fans at the time, so visiting The Met was especially fun. It was one thing to see these places on television, but seeing them in person made everything feel a little more real. XOXO
My Friend Became My Personal New York Tour Guide
One of my favorite things about visiting New York with my friend is that I never had to figure everything out myself. She already knew the city, so I could just follow along and enjoy the experience. We walked around Manhattan, explored Brooklyn, wandered through Chinatown, and stopped at some of the places I’d seen in movies and television shows.
We even went to a rehearsal taping of The Tonight Show Starring Jimmy Fallon, which was such a cool experience. I’d never been to a television taping before, so getting to see how everything worked behind the scenes was a fun addition to the trip. Also, I’ve loved Jimmy Fallon since his days on SNL 🙂
And because my friend knew I loved movies and TV shows, she also made sure to include some stops that felt like little pop-culture pilgrimages.
New York Through Movies and TV Shows
One of my favorite stops was FAO Schwarz. I’m a huge fan of Big starring Tom Hanks, so naturally, I had to see the famous giant piano.
Getting to recreate that little movie moment was such a cool experience. It’s one of those things that might seem small to someone else, but when you’ve loved a movie for years, actually standing in a place connected to it makes the experience feel special.
We also visited Logos Bookstore, the small bookstore in New York that was used as Mooney’s bookstore in the Netflix series You. (Hello, Joe!) The bookstore itself was small and quaint, but that was part of the charm. Of course, I had to go inside. We also made a stop by the apartment building featured in the popular show, Friends. Kind of a must!
Between Gossip Girl, Big, You, Friends, and The Tonight Show, these trips made me realize just how much of New York City I’d already experienced through a screen before ever visiting.
There’s something really fun about recognizing a place you’ve seen in a movie or show and suddenly realizing, Wait… I’m actually here.
My First New York Subway Experience
Another first from that trip was taking the New York City subway.
Coming from Atlanta, I’m familiar with MARTA, but I’m much more accustomed to seeing the train above ground. New York was a completely different beast because so much of the city happens underneath the streets. At first, I wasn’t sure what I was doing.
Eventually, though, you realize that the system isn’t quite as intimidating as it seems. Follow the signs, pay attention to where you’re going, and eventually you’ll figure it out.
The streets were another story. I understand the logic behind the numbered streets, but I’m still personally not a fan. LOL You’ll hear something like “16th and 24th West blah blah blah” and I’m standing there thinking, Okay… and where exactly am I supposed to go?
I’m also from the South, where we’re generally pretty friendly and smiley, so I’d heard the running joke that you have to “look mean” when you’re walking around New York, especially as a woman. That’s not exactly my natural personality. I’m used to smiling at people and saying hello. New York definitely taught me to be a little more aware of my surroundings while navigating a huge, unfamiliar city.
Come Hungry: Pizza, Cheesecake & More
Food is a huge part of the New York City travel experience. You can’t talk about New York without talking about food.
Everyone has their favorite pizza spot, and while Joe’s Pizza is one of the popular choices, my personal favorite was actually L’Industrie. That pizza was so good.
And then there was the cheesecake. Junior’s. Also delicious. Between the pizza and cheesecake alone, I understood why food is such a big part of the New York experience.
On my most recent trip, I also got to try something completely new to me: an omakase-style dinner at Tsumo Omakase. I’d never experienced omakase before, so watching the chef prepare the different types of sushi right in front of us was part of the fun.
And yes, it was delicious.
We also stopped at Pop Up Bagels, because apparently I was determined to eat my way through New York one iconic food at a time. LOL
The New York Sights That Stayed With Me
Some of the places I’ve visited over my four trips are the kind of attractions you expect to see when visiting New York, but that doesn’t make them any less memorable.
The Brooklyn Bridge was one of those places. There’s something surreal about seeing the New York City skyline while standing on the bridge instead of just looking at pictures of it.
On my most recent trip, my friend and I also visited the Manhattan Bridge and arrived just in time to watch the sunset behind the Manhattan skyline. If you’ve been following Travel Britten for a while, you already know I have a thing for sunsets. LOL
And this one did not disappoint. The sky, the skyline, the water, and the city all coming together at the same time made for one of those simple travel moments that sticks with you. We also spent some time at Hudson River Park, which gave us another chance to slow down and take in the city without constantly rushing from one attraction to the next.
Visiting the 9/11 Memorial
The 9/11 Memorial was a very different experience from the rest of the trip.
For New Yorkers, and Americans in general, September 11th is a day we’ll never forget. Even if you weren’t in New York when it happened, the events of that day are part of American history that most of us remember in some way, shape, or form.
Visiting the memorial felt like an important stop to make. Seeing the names of all the people who lost their lives that day was difficult. Standing there and seeing so many names together made the scale of the tragedy feel much more personal.
It was one of the most memorable parts of my first trip to New York, but also one of the heaviest. Not every travel memory has to be fun to be meaningful.
Stranger Things on Broadway Was Incredible
One of the biggest surprises from my most recent New York City trip happened on Broadway. My friend surprised me with tickets to see Stranger Things: The First Shadow. If you know me, you know I love Stranger Things, so I was very excited.
And honestly? It did not disappoint.
The cast and crew were fantastic, but the special effects were what really stood out to me. The lighting, smoke, sound effects, and set design were incredibly well done. You could tell that a lot of thought went into making the production feel like the world of Stranger Things rather than simply putting the characters on a stage.
The transitions between the real world and the Upside Down were especially impressive. The lighting and sound made it immediately obvious which world you were in, and seeing those transitions happen live was completely different from watching something like that on television.
There was so much attention to detail that, for a moment, it almost felt like I wasn’t watching a play at all. I was inside the show.
10/10 highly recommend! *NOTE: The show is set to close on January 3rd, 2027, so get your tickets while you can!*
A Beach Day in Queens? Yes, Really.
My visit this past July gave me another side of New York that I hadn’t really experienced before: Rockaway Beach in Queens.
We took the train out to the beach, and even the ride there was part of the experience. I got some great views of the water along the way, and as we got farther from the city, everything started to feel a little less hectic. Once we arrived, it almost felt like we weren’t in New York anymore.
Almost.
There were beach bars playing music, people watching World Cup games, groups hanging out, and plenty of people enjoying the summer weather. So it definitely had a party atmosphere.
We grabbed some snacks and drinks, brought a speaker to listen to music, and eventually found a quieter spot where we could put down our towels and actually relax. It was such a nice change of pace from spending the day surrounded by skyscrapers and crowds.
Sometimes you need a little beach break in the middle of a city trip.
New York Was Expensive… Especially After Living in Europe
One thing I definitely noticed during my latest visit was how much more expensive New York felt after living in Europe for the past two years.
I had just come from Gran Canaria, and let’s just say Europe had gotten me a little too comfortable with lower prices and not having an extra tax magically appear when I reached the register. LOL
No matter where I am, I’ll probably always complain about prices in the United States. But New York? Yeah… I noticed. I honestly don’t remember exactly how much I spent on the trip because my friend was incredibly generous and paid for a lot of things. But the difference in prices was still noticeable.
It was a funny little culture shock coming back to the U.S. after spending so much time living in Europe.
The World Cup Made New York Even More Crowded
My July visit also happened during the FIFA World Cup, which added another layer to the city’s already busy atmosphere.
The World Cup final between Spain and Argentina was held at New York New Jersey Stadium on July 19, 2026, so the city was full of international visitors and football fans around that time and you could definitely feel it. There were people everywhere.
New York is already crowded, but when you’re walking through a sea of people and can barely move, it can become a little overwhelming. At the same time, there’s something fun about seeing so many different people and cultures coming together in one place.
It just wasn’t necessarily the peaceful summer vacation atmosphere I might have imagined. I’m also not a soccer fan, so the event itself meant nothing to me. LOL
What Four Trips to New York Taught Me
After four visits, I still don’t think I’ve experienced everything New York has to offer. Honestly, I’m not sure that’s even possible. But I have learned a few things:
New York is expensive. Maybe that seems obvious, but living in Europe for two years definitely changed my perspective on American prices.
New York is crowded. Sometimes that’s part of the fun. Other times, you just want everyone to move approximately three inches to the left so you can breathe. LOL
The subway is manageable. It might seem overwhelming at first, but once you follow the signs and understand where you’re going, it’s much easier.
The numbered streets are still confusing to me. I’m sorry. I said what I said.
And perhaps most importantly, New York can feel completely different depending on where you are.
Manhattan, Brooklyn, Chinatown, Hudson River Park, and Rockaway Beach all gave me different impressions of the city. That’s probably part of what makes New York so interesting. You’re not really experiencing just one city. You’re experiencing a bunch of different neighborhoods, cultures, environments, and personalities all packed together.
Would I Visit New York Again?
So after four trips and plenty of New York City travel memories, would I go back? Yes. But there’s a catch.
To visit my friend specifically? Absolutely. She’s been the common thread through all of these trips, and having someone I know and trust in the city makes the experience completely different.
To fly to New York by myself for no particular reason? Probably not. LOL New York isn’t necessarily a destination I feel like I need to check off my list again just for the sake of saying I’ve been there.
But that’s okay. Some places become special because of the people you experience them with.
My multiple trips to New York have given me a pretty random collection of memories: an eight-degree January night at a Jesse McCartney concert, exploring Central Park and The Met, recreating a Big moment at FAO Schwarz, eating amazing pizza and cheesecake, seeing the 9/11 Memorial, watching Stranger Things come to life on Broadway, catching a sunset over Manhattan, relaxing at Rockaway Beach, and navigating a city that somehow still confuses me with its numbered streets.
Four trips. Four very different experiences.
And maybe that’s what keeps bringing me back!