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?
In South Africa doing lots of boat stuff. Departure north from Cape Town around December 15th. Arrival in the Caribbean around the beginning of February, after 5300 miles or so.