Most from NY or
New England elect to
work their way down to
Hampton Roads, VA or
Beaufort, NC before heading offshore. The
Gulf Stream is narrower there, 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. If you depart
Hampton Roads mid-day, you'll be across the Stream SSE of Hatteras by sundown the next day. The next front will pass over you and 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 toward Bermuda before turning south will add about a day to the
passage.