Whew, this one was HARD. This post is for the fearless, the adventurous, the families who thrive on organized chaos – especially the kind that comes with wrangling five energetic boys under ten in the heart of New York City! I’m Diana, a full-time entrepreneur, a part-time circus ringleader (affectionately known as “Mama” to my crew), and a firm believer that the best education is one filled with exploration as I’ve already written in this post Unleashing Curiosity: Adventurous Learning.
Now, some might look at a Manhattan adventure with five little hurricanes and think, “disaster!” But let me tell you, with a well-planned itinerary, a healthy dose of “go with the flow” attitude, and reinforcements in the form of my partner in crime, Luis, and my mom, affectionately known as Mimi, the Big Apple can be the most epic adventure for your tiny squad. We just wrapped up a whirlwind extended weekend there with my boys – ages 2, 5, 7, 8, and 10 – and not only did we survive, we thrived! Here’s the lowdown on how we conquered the concrete jungle, keeping everyone (mostly) sane and having a blast along the way.
Day 1: Welcome to the City That Never Sleeps (and Neither Do We!)
We touched down at Newark airport in New Jersey in the early afternoon, feeling the familiar travel buzz and excitement for the adventure ahead. A quick train ride from Newark landed us at NYC Penn Station, and as we climbed the subway stairs up to the surface, their shock and awe was the best feeling in the world! They couldn’t stop shrieking and pointing at how high the buildings were, the amount of people everywhere and the lights and sounds that surrounded us just outside of Times Square.
After a short walk, we reached our home base – The Wyndham Tryp Hotel. The boys were bouncing off the walls with excitement, so we decided to hit the ground running (literally!). Our first mission: experiencing those iconic Manhattan skyscrapers. We wandered around Midtown, marveling at the towering giants and soaking in the electric city vibe.
Dinner was a must, and what better way to celebrate our arrival than with a classic New York burger? We found a fun, family-friendly spot with juicy burgers, crispy fries, and milkshakes that disappeared faster than you can say “Big Apple!” Refueled and ready for more, we strolled over to Bryant Park, a hidden gem in the middle of the urban jungle. The highlight? A magical ride on the iconic carousel – a perfect way to end a jam-packed first day.
Day 2: Lady Liberty, Baseball, and a Bit of a Splash
Day two was all about iconic experiences and embracing the unexpected. We started with a subway ride to Battery Park, where we boarded a ferry to Lady Liberty. We opted not to climb the crown (too many steps for our little crew!), but even seeing Miss Liberty up close was awe-inspiring. The boys were particularly fascinated by the size of the ferry, spotting landmarks and yelling “Look, Mama!” at every turn.
After our brush with history, we needed some playtime. Thankfully, Battery Park has a fantastic playground that kept the boys entertained for ages. Climbing structures and the fastest metal slides – it was the perfect way to burn off some energy. Walking back to the subway station, we grabbed fresh fruit and delicious smoothies for a healthy post-play refuel.
After getting back to the hotel and getting Mimi and Baby Jack settled in for the evening, our next stop was Yankee Stadium! If you a friend to this blog, you know that the four big kids are OBSESSED with baseball so this was a highlight for them. We settled into our seats, hot dogs in hand (a must-have at any baseball game, right?), ready to cheer on the Yankees against the Twins.
Little did we know, Mother Nature had other plans. A rain delay turned into a downpour, testing our patience and flexibility. But the boys, surprisingly, didn’t mind one bit. Our seats were just under the balcony of seats above us, keeping me and Papi dr, while the boys decided to run through the now empty, soaked seats, playing tag and just dancing in the rain. The game finally resumed, stretching late into the night, but the boys were troopers, staying enthusiastic until the final out (a Yankees win, of course!).
Day 3: Central Park – A Playground Paradise
Day three was dedicated to the green oasis in the heart of the city – Central Park! We spent the whole day exploring this massive urban wonder. Imagine: endless paths to walk, vast stretches of green grass for running, and giant natural rocks perfect for climbing. The boys were in heaven! We hit all the big playgrounds – Heckscher Playground, Bil ly Johnson Playground, and Adventure Playground – each offering unique challenges and opportunities for imaginative play.
Another carousel ride added to the fun, and of course, no trip to Central Park is complete without climbing as many rocks as possible. Thankfully, the afternoon brought sunshine, allowing us to cool off in the refreshing spray pads. Laughter, screams of joy, and maybe a few scraped knees later, we refueled with delicious ice cream from a food truck (melting all over the boys, naturally, adding to the post-adventure charm).
On our 2 mile walk home (yes, the boys WALKED back!), we stopped by On Top of the Rock at Rockefeller Center and it had the most AMAZING views. And our sky-high sightseeing wouldn’t be complete without experiencing… The Beam! I’m sure you’ve seen the iconic 1932 photo depicting 11 ironworkers lunching precariously on a steel beam, 69 stories high? Well, it was taken right there during the construction of 30 Rockefeller Plaza and yes, you get to sit on a beam, it raises up high from the 69th floor and turns you around for a full view of the city. It was breathtaking!!
Exhausted but exhilarated, we called it a day, returning to the hotel for a well-deserved rest. That evening, however, wasn’t for the faint of heart. With the four older boys (Papi deemed the 2-year-old too young for this one!), Mimi and I ventured out to see the magic of Harry Potter and the Cursed Child on Broadway. The sets, the costumes, the special effects – it was a sensory overload in the best way possible. The boys were mesmerized by the story, and even the late night couldn’t dampen their excitement. They claimed this was one of their favorite parts of the entire trip.
Day 4: Sweet Treats & Broadway Dreams
Day four started with a bang – breakfast at Ellen’s Stardust Diner! This quirky spot is famous for its singing waitstaff, and let me tell you, they can belt out a tune! The boys were wide-eyed as they enjoyed their pancakes while being serenaded with show tunes. Fueled by a sugar rush and the energy of the diner, we headed back to Central Park for another round of playground fun and rock climbing. They couldn’t get enough of the wide-open spaces and endless challenges.
In the afternoon, we decided to indulge in a truly unique experience – the MUSEUM OF ICE CREAM! This whimsical haven was a dream come true for the boys (and maybe even some of the adults!). Interactive exhibits, colorful rooms, and of course, an endless supply of ice cream – it was a sugar-fueled adventure they won’t soon forget. The highlight? A giant pool of sprinkles at the end, where they could dive in and create their own ice cream masterpiece. The sticky mess was totally worth the smiles on their faces.
Dinner was a casual affair, with us grabbing various delicious options from different food trucks. We wandered around the city, soaking in the sights and sounds, and enjoying the diverse culinary offerings that New York has to offer.
Day 5: Farewell, Big Apple!
Our last day in Manhattan was bittersweet. We started with a classic New York breakfast from a local deli. With full bellies, we took one last walk around the city, marveling at the towering buildings we had come to know and love. It was amazing to see how much the boys had grown accustomed to the hustle and bustle, confidently navigating the sidewalks and soaking up the city vibes. Even baby Jack spent the entire trip walking the streets, refusing to sit in his stroller. With a bit of patience on my part, it truly was an experience for him to be part of the “big kids” in the Big Apple.
The train ride back to the airport was filled with chatter and reminiscing. They were already asking when we could come back and explore more. Looking back, it was a whirlwind adventure, filled with laughter, unexpected challenges, and memories that will last a lifetime. Sure, there were moments of meltdowns and melty ice cream, but the joy of seeing my boys experience the magic of New York City far outweighed any minor hiccups.
So, remember, while these types of cultural experiences are exhausting on us, our little ones learn more in these adventures than any book could teach them. And just know, conquering the concrete jungle with your little ones is possible! With a little planning, a lot of flexibility, and a whole lot of love, you can create an unforgettable adventure for your family, just like we did. Now, get out there and explore! The Big Apple is waiting!
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