On Friday morning, at 2:49 AM, the alarm went off. This was a few minutes before the rest of the team woke up. The night before, we all set our alarms for 3 AM to ensure that no one overslept. There was a great adventure that lay in store and I wanted a few extra minutes of time to appreciate it. I set my alarm to go off a few minutes earlier in order to be ready for the wake up. The few minutes represented “my time”; it was just a little bit of quiet before the chaos ensued.
Hours 1 – 24 (Friday)
Just as planned, exactly at 3:00 AM, a beautiful cacophony of iPhone ringtones began to play throughout the house. It was finally time to leave!
The boys rolled out of bed, and Mama greeted us with her typical hugs and enthusiasm. The dogs were confused – it was the middle of the night. A few minutes later, Jackson, John and I set out for the Tampa International Airport with only our backpacks, the ones we packed the night before. Our flight’s departure time was at 6 AM. We didn’t have a full itinerary, but we knew our destination – New York City.
On the way to the airport we listed to loud music and sang. The Truck Songs playlist is one that I’ve had for many years. It’s the boys favorite playlist from when they were about 5 & 3 years old. We sang loudly and laughed – Jackson and I imagined John taking the lead in The Lion Sleeps Tonight by the Tokens – “weeeeee, weeeuhhhh weeeuuhh the Lion Sleeps Tonight!!!!!!”. It was a thrilling ride to the airport in the middle of the night.
We landed at JFK around 8:30 AM and trusted Jackson to get us from the airport to Manhattan. Our target was Penn Station, which ultimately became our hub of sorts, for the entire trip. None of us had ever traveled via the NYC subway or train system, so we were excited and nervous to figure it out.
A little foreshadowing: by Sunday, we felt like train experts!
We followed the crowds and the signs out to the AirTrain platform and rode the shuttle from JFK to the Jamaica Station. From there, we took the LIRR (Long Island Rail Road) into Penn Station. Easy! At this point of the trip, about 9:30 AM, neither one of the boys had seen the skyline of Manhattan yet. It was finally time. The anticipation had been building for weeks, and now was the time to go see the big city.
Let the adventure begin. We were going to try to see it all…by Sunday afternoon!
We made it!
We walked from Penn Station up up to Times Square, stopping along the way to see The Red Caboose. the Lego Store and FAO Swartz in the Rockefeller Center.
As you’d expect, we saw some very odd things along the way. The main thing I wanted in this trip was to be fully present with these young men, as their loving wingman, during their first exposure to the crazy NYC occurrences you run into when visiting the big city.
Best Pastrami Sandwich In The World
Eventually we made it to Carnegie’s Deli for a sandwich – after a delicious pastrami rueben, it was across the street to Central Park.
Central Park
We climbed on some rocks and walked over to the Bow Bridge for some pictures.
We walked down the mall and hit a few stops along the way to check artwork and other merchant booths. It was a beautiful, hot summer day in Central Park.
To The Hotel
The early start and the heat was beginning to catch up with us. We made a decision to head to the hotel and refresh for a few minutes. We were carrying our backpacks and decided it was time to head to the Homestead Suites, at 312 W 37th Street – for checkin. A nice walk down 5th Avenue was in order.
We got to the hotel a few minutes before 4 PM and headed to our room. The cool AC and the soft beds were calling our names. A brief nap was a perfect way to recharge and refresh us after our long travels. And by brief, I mean 2.5 hours 🙂
We woke up a little after 7 PM and decided to go find some dinner. We thought NY Pizza would be a great way to kick off the trip, but after some reflection and negotiation, we decided Italian in Hell’s Kitchen at a sit down place would be a better way to start off the trip. We chose Nitti’s at the corner of 39th and 9th.
We enjoyed the meal and the conversation about the 1st day. And we set the plan for the next morning. 9/11 Memorial by subway would be our first stop.
After dinner it was time to head to Times Square for a stroll and to see the night life. Wow! What a way to end the day.
We stopped at the M&M Store and got some custom candies. “J&J&J&J”, “J&J&J&J& Lurghts” and one of Mama 🙂
Around 11pm, we decided that was enough for the first day and headed for the hotel for some sleep.
Hours 25 – 48 (Saturday)
We woke up a little later on day 2 – about 5 hours later. We got started at 8AM and headed down for the hotel breakfast. This was the meal the boys were most excited about!! We had dinner the night before in Hell’s Kitchen and we were in NYC, literally anything you could possibly want from a culinary standpoint, and they could not wait to hit the hotel lobby for breakfast. I love them so much!
After breakfast, it was off to Penn Station to find our train down to the financial district and to see one of the top planned destinations of our trip – the 9/11 Memorial.
Subway Ride #1
The funniest part of the first subway ride was I got us on the wrong train! We were headed south, and instead we actually jumped on a train headed north. It wasn’t until the 1st stop that Jackson realized we were headed uptown that we realized it.
“Dad, I think we’re going the wrong way. This is the Times Square stop.”
Doh! Let’s switch.
Our first big lesson on the subway: make sure you get on the right train.
The (correct) subway ride was about 20 minutes and filled with “NYC character”. There were people staring blankly at their cell phones and a homeless man laid out on the train bench wailing while he tried to sleep. He was partially clothed and didn’t seem well. I could tell from the boys’ faces (especially John’s) that this was very uncomfortable. They didn’t know what to do. It was really their first time seeing a scene like this – a homeless man crying for help, or what seemed like a cry for help, and no one coming to their aid. We had a chance to discuss it in real time while on the ride. I didn’t have all of the answers, but I did think it was the right thing to do – discuss the situation in an open and specific way. We talked quietly, a little above a whisper, about what we knew and what we didn’t know. We realized that the man was certainly facing a tough life, but we weren’t sure why. Did he want to be there? Did he need medical attention? Was he on drugs? Did he have mental illness? We didn’t know, but we did discuss it and we discussed ways we might help. We also discussed how we weren’t going to judge him for things we didn’t know for fact. Ultimately, we said a prayer for peace and wished him well. It felt like an important part of the trip.
We came to our stop at the WTC and walked up the subway stairs headed for the 9/11 Memorial. A little later, we were able to discuss how the 1993 bombing of the World Trade Center may have hurt people much like us on that day. It was pretty deep to think about.
We toured the WTC and 9/11 Memorial for about 3 hours. Wow. What an amazing tribute to that horrible event. I’d recommend to anyone who hasn’t been to go. It’s an amazing story and a very well done tribute to those who died. I cannot imagine what it would feel like to have a loved one who died that day, but I think the memorial beautifully honors those who were lost. It was somber and with sadness, but respectful and hopeful.
Wall Street
After our tour of WTC, we headed down the financial district to Wall Street. We had to have some more delicious NYC Pizza, so we stopped for a few slices. Then back to the street as we headed down to the water with a goal of seeing the Statue of Liberty.
We stopped at the NYSE and Trinity Wall Street parish. The bishop of the diocese that we consider home, Diocese of Florida, was the rector at that church during 9/11.
What a complex intersection of ideals in this photo – finance & faith.
As the rain started to fall, we decided to get some umbrellas. We each had our own and this made the rain much more tolerable. We got a little wet, but it was OK with all. As we prepared for our ferry ride, we took a good look at the Brooklyn Bridge from the street, and of course we got some ice cream from a shop near Pier 17.
This was the photo of the trip, some rain and some nerds 🙂
At about 2:30p, we were able to board the Liberty Cruise. We were one of the first ones on, so we had our choice of seats. After trying a few options inside, we settled for a few outside seats under the overhang.
The ride was about 1 hour and it was narrated. I enjoyed the narrator. He knew the city, but he also knew when to stop talking. As we rolled through the downtown landmarks, he was informative on pointing out the lesser known points of interest. But, when we got to Lady Liberty, it was noticeable how he stopped talking and let her tell the story. It was a great ride.
Lady Liberty
After the cruise, we jumped into a Lyft for a ride back to the hotel. I wanted to hustle back to allow us to get cleaned up, and also not get any wetter than we already were. We had a big night planned and time was of the essence. So we headed back to the hotel, arriving around 4:30p.
After some showers and a fresh set of clothes, we were back out the door headed to Penn Station again. We were a little more confident in our ability to navigate the subway, now that we had one successful one-way trip under our belts. This trip was going to really test us though. What were were told sounded simple: “Take the 4 to the shuttle, one stop, get off. Take it one stop over. Get on the 6 train to 161.”
Got it.
And we did just that. We actually had no issue, just like the other million plus people who rode the subway that day. About 5:30p, we walked into Yankee Stadium, as the Boston Red Sox were in town.
New York Yankees vs. Boston Red Sox at Yankee Stadium in the Bronx
We did it all. We had a value bucket with chicken tenders and french fries, commemorative NYY cups, the coach got thrown out of the game and there were lots of runs scored. While the Yankees didn’t win (final was 11-7) the experience was amazing.
After the game, we rode the subway back, and opted to get off at Times Square to walk the last leg. If you get a chance, ask John about the subway ride home. Let’s just say, it was tight. Like, “sardine can” tight.
We stopped and grabbed a bag of burgers from White Castle for a (literally) midnight snack and took them back to the hotel before a few hours of sleep, because “we’re health conscious”.
That was what we did Saturday 🙂
Hours 48 – 71 (Sunday)
Hours Touching the Sky: Our Final Day at the Empire State Building
Sunday morning arrived with a bittersweet feeling—it was our last day in the city, and we knew we had to make it count. With the end of our trip approaching, we had one iconic destination left on our must-see list: the legendary Empire State Building.
Starting our morning on 37th Street, we made our way south through the bustling Manhattan streets. The short walk down to 34th Street felt charged with anticipation. After all, this wasn’t just any building—this was the Empire State Building, the Art Deco masterpiece that has been capturing imaginations and defining the New York skyline since 1931.
The Ascent
Once inside, we joined the steady stream of visitors making their way to the elevators. The ride up to the 80th floor was an experience in itself, watching the floor numbers climb higher and higher. When the doors opened, we found ourselves at the observation level, surrounded by panoramic windows offering glimpses of what was to come.
But we weren’t done yet. Another elevator awaited to take us even higher—all the way up to the 86th floor. This is where the real magic happened.
A View Like No Other
Stepping out onto the outdoor observation deck felt like entering another world entirely. The city sprawled endlessly in every direction, a magnificent tapestry of steel, glass, and life unfolding 1,050 feet below our feet. From this vantage point, the urban canyon of Manhattan transformed into something almost abstract—yellow taxi cabs became tiny dots, people turned into moving specks, and the geometric patterns of the city blocks created a mesmerizing urban quilt.
Looking north, we could trace the green ribbon of Central Park cutting through the concrete jungle. To the south, the harbor stretched toward the Statue of Liberty. East and west, the city seemed to extend forever, disappearing into the horizon where buildings met sky.
Back to Earth
Once we emerged onto the sidewalk, we couldn’t resist the urge to crane our necks and look back up at the towering giant we had just conquered. From street level, the Empire State Building seemed to stretch impossibly high into the sky, its limestone and steel facade disappearing into the clouds above. It was hard to believe we had just been up there, looking down at the very spot where we now stood.
Don’t Forget To Send A Postcard
While in NYC, we remembered to send a note to some loved ones. Mommom and Poppop got a card from the 3 boys on their adventure.
Standing there in the heart of Manhattan, surrounded by the energy and rhythm of the city, we felt that familiar New York hunger calling. What better way to celebrate our sky-high adventure than with another slice of authentic New York pizza? We found a local spot and savored every bite, the perfect fuel for our continued exploration.
After satisfying our appetites, we decided it was time for some souvenir shopping and made our way to a New York tourist store to find some special things for mommy back home. We weren’t disappointed—the store was filled with classic New York memorabilia. We carefully selected a New York t-shirt, a coffee cup, and several other interesting items that would serve as perfect reminders of our amazing adventure. It felt good to know we’d be bringing home tangible pieces of the city to share.
Time to Say Goodbye
At this point, we all agreed it was time to head to the airport. While our flight didn’t leave until evening, we figured we would sit in the airport and reminisce about our incredible trip to the big city. The adventure was coming to an end, but the memories were just beginning to settle in.
We hustled back to the hotel to grab our bags, then made our way back to Penn Station one final time. By now, we had become experts on the Long Island Railroad route—the train to Jamaica Station, the transfer, and then onward to JFK Airport. What had seemed daunting just days before now felt like second nature. We navigated the familiar route with confidence, arriving at the airport with no delays.
While waiting at the airport to depart, we had a slight delay due to mechanical trouble on the plane. We all agreed that it was good to find this out on the ground instead of in the air.
Eventually, we found ourselves boarding the airplane, settling in for the flight back to Tampa International Airport.
As the plane lifted off and New York’s skyline disappeared below us, it was hard to believe everything we had experienced in just under 71 hours.
A Trip of a Lifetime
Looking back, this whirlwind adventure to the Big Apple was truly a trip of a lifetime—one that we will never forget. From conquering our fears on the subway system to standing atop one of the world’s most famous buildings, every moment had been filled with discovery, excitement, and the kind of memories that last forever.
Without a doubt, this was an incredible journey— and just the beginning of our relationship with the city that never sleeps.