But he was certainly used to that route. In 15 years of flying, I can't think of anywhere I've flown 35 times, let alone five of them at night. Kennedy had made all of those trips within the past 15 months. I think his familiarity with the route probably balanced out his lack of solo flight time and training, on a calm, fairly clear night. So here's the picture.
Pilot confidently plans a routine hop to a familiar airport on a fairly clear day.
Then he starts running a little late. No big deal, the darkness, since his recent night flights included Vineyard landings. It's a wedding, for crying out loud, not exactly something to be late for. Then he gets up in the dusky sky and flies out over Point Judith, out to sea. Unexpectedly, he can't see the lights of the island.