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?
Back in the water in Grenada - with new main and #2 and cockpit canvas (Santa came early). Will spend the winter and early spring in the Caribbean and then head to Bermuda and the northeast US. Still trying to decide if we will bring the boat to Canada, either in 2015 or 2016.