I have only spent a few weeks in St Thomas so take this for what it is worth. If you are into the cultural activities to be found in Philly let along NYC, you will be very disappointed. The weather and sailing are great and I imagine the people are friendly (seemed to be when we there), but the cultural activities?? How about Hawaii for warmth, US flag, decent sailing?
Finished the circumnavigation in early February in Grenada. Have to work on a book project for the next several months so the boat will be waiting for next year.