Spring break doesn’t always mean everyone has same itinerary. In the Kaplan household, it often means divide and conquer. This year, that meant a father-son trip east while the rest of the crew held down the fort. With Elan back in school, Jack (12) and I had an extra week to work with, and we decided to take it to New York.
I always thought Jack would enjoy New York City. The energy, the scale, and the variety of things to do seemed like it would excite him. In taking a one-on-one trip, the logistics would be simpler; fewer competing preferences, just time together and a loose plan. In our case, that plan centered around sports, food, and a lot of walking, all anchored out of Midtown Manhattan.
We stayed at the Hotel Martinique New York, which was central enough to get anywhere quickly, but not in a pocket that felt chaotic or sketchy. It also had a decent gym, which in theory was going to help offset some of the eating.
Day one set the tone. We arrived in time for dinner. Jack, a self-proclaimed pizza connoisseur, had one priority: New York pizza. We delivered on that quickly, then walked to Times Square to take in the full sensory overload. On the way back, we made what can only be described as a questionable transportation decision; jumping into one of those bike carts clearly designed for a romantic couple, not a father and his 12-year-old son. Eleven minutes later, mostly spent sitting in traffic, we were out $107. Consider that a public service announcement.
The next day, we took the subway up to the Bronx for a day game at Yankee Stadium. As soon as we got in, he made a beeline for the wall to try to get player autographs. Sitting third row was incredible. Being that close to the action is the kind of experience that overrides everything else. And then came the moment he’ll remember for a long time; a ball tossed into the stands by a player that somehow ended up in his hands…after briefly going through mine.
One thing I was a little unsure about was navigating the subway, which when unfamiliar with the stations, has always stressed me out. Everyone seems to be in such a hurry and there never is clear enough signage. Do I have the right ticket? Am I on the right platform? Jack had an instinct for it (where to go, how to get back) that was noticeably better than mine. I was very impressed watching him figure out a new environment in real time and eventually lead the way.
The next night, we met up with my college buddy, Ron, and his son at Madison Square Garden for a steakhouse dinner and Knicks game. There’s a built-in nostalgia to those meetups; friends from another chapter of life, now sitting side by side with our kids, watching them take it all in. Madison Square Garden lives up to its reputation. The energy is constant, the crowd is engaged, and the celebrity sightings were intriguing. It’s one of those venues where the experience goes beyond the game itself.
The weather warmed up and a couple of mornings were spent electric biking through Central Park, which turned out to be one of the highlights of the trip. It’s a different perspective of the city; less chaos, more space, and just enough freedom for a 12-year-old to feel like NYC is his own personal playground.
Of course, we made sure to lean into the food scene. One of our spots was Tony’s Di Napoli, my longtime favorite for classic, family-style Italian. If you’ve been, you know the deal; you order with confidence and then immediately realize you’ve committed to far more food than necessary.
At one point, we struck up conversations with the tables on both sides of us, which feels very on-brand for a place like that. One of them, a mother and daughter, also over-ordered and offered us some of their shrimp scampi. Despite the fact that we already had more food than we could reasonably handle, I accepted. Three shrimp. No regrets.
After dinner, we made the obligatory evening lights trip to the Empire State Building. On floor 102, I got an email that a buyer had accepted a counter offer for one of my listings back home. Opening escrows from 1,250 feet up felt fitting; New York energy meets Los Angeles business. Talk about being on top of the world!
On our last day, Jack started browsing apartments for him to live in after college, which feels both premature and exactly right. He didn’t need to tell me he had a great time; I already knew.
Looking back, what stands out isn’t any one moment, it’s the rhythm of the trip. The conversations walking between places. The small decisions such as where to go next, what to eat, how to get there. The joy of seeing your son’s curiosity and excitement in experiencing a new place. When it’s just the two of you, those moments carry a little more weight.
