Most from NY or
New England elect to
work their way down to
Hampton Roads, VA or Beaufort, NC before heading offshore. Mark is right--Beaufort is a better port to leave from, but it will take you three days in the ICW to get there from Norfolk.
However you get there, ICW or offshore, the Gulf Stream is much narrower off Hatteras, and you can get across it in 12 hours or so. Jumping off from VA or NC also minimizes your exposure to the inevitable gales that you'll encounter. If you leave from NY you'll likely experience two or even three gales before getting far enough south to be out of their reach.
Cold fronts come off the
East Coast every 3-5 days in early November. Wait until one passes, then
head out in the light southeasterlies that follow, motor-sailing for a while if necessary until the
wind begins to clock in advance of the next approaching front. Hatteras has a fearsome reputation, but if you depart
Hampton Roads at mid-day, you'll be across the Stream SSE of Hatteras in relatively settled conditions by sundown the next day. It will probably be cold for that first day and night, although not bitterly so. It warms up quickly once across the Stream.
After you've crossed the Gulf Stream, the next front will pass over you. The
wind will clock through the SW and build as the front approaches, becoming NW, N and NNE or NE at gale force. You can get a nice ride on the NNW to NNE winds that come with it. A very strong front will push you right through the Horse Latitudes to the Tradewinds, so you won't have to
motor in calms.
We've been successful sailing pretty close to, or a bit north of the rhumb line. From Hampton Roads to Tortola is about 1380 nm. Heading substantially toward
Bermuda before turning south will add about a day to the
passage.
Besides a good source of weather forecasting, consider getting a Gulf Stream
forecast, which will show where the narrowest
parts are, but equally important, where the cold eddies SE of the Stream will be. You can plan your course to use the 1-2
knot eddy currents to your advantage. If you get headed by an eddy, you'll really slow down.