We went to New York at the beginning of this year and we had the best time just wandering and exploring the city together. It was the longest flight we had taken with Holden and he did amazingly. He slept the entire way on the red eye to NYC and then for half of the flight on the way back home, and when he was awake he was perfectly content to color and read in his seat. We had been slightly nervous about the five hour flight and how he would feel being in a foreign place for a longer period of time, but we all had so much fun that we started planning our next trip as soon as we returned home.
We didn't make any real plans for our stay beforehand and I loved our ability to go somewhere on a whim or last minute recommendation. There was so much to see in New York and I felt like we were barely able to scratch the surface regardless of nonstop exploring for several days on end and I foresee many more trips to this magical city in the future.