Clearing In - Why? This is the USA. The easiest country in the world to just walk into and/or stay illegally .............no worries mon
A little more seriously, sure he's not the 1st sailor coming into NY/NJ area...........as with many voyages = preparation, timing, weather & planning will make the difference. Or as an alternative, a stop at another port (if necessary) to clear in will not ruin his overall goal of Jersey to Jersey. But AIS + radar would be very helpful & pay dividends here.