> People should just jump in with both feet, and head south offshore... Most will realize by the time they get to Bermuda they're not
> cut out to Live The Dream, and might save themselves a lot of time and money in the end...

... you're supposed to aim for Bermuda and miss. Turn right after crossing the Gulf Stream and just head south. 8 - 12 days (ish) from Norfolk to Tortola. Maybe 6 or 7 to the Bahamas.