There is a huge influx of boats through Annapolis in early October. That would suggest a late September departure which should give you a little wiggle room to pick your window for the pretty long offshore jump at New Jersey. The offshore jump speeds things up a bit as you will pretty much need to do that in one shot. You are somewhere around a week north of Annapolis.
I think that you will need every bit of the time and then some between now and the end of September to commission, upgrade and shake things down.