I wouldn't go out there at the end of August. I rode out a hurricane some years back in Florida, and I won't be doing that again!
Hurricanes are unpredictable. You won't be able to move out of the way; they're too fast, too big, and they're knuckleballs.
As soon as you get a few days north the frequency goes WAY down. North Carolina is not Florida, and the Chesapeake itself sees few hurricanes; generally they are tropical storms by then, if they do not simply skip off-shore. To be honest, while you are in the Bay you may avoid a boomer back home in Georgia! The Bay gets few strong storms, and really none that cannot be ridden out at a sheltered marina (one that DOES NOT open straight to the Bay, like Herrington Harbor North) or good hurricane hole.
Selkirk is right about avoiding hurricanes in Florida; they often get 2 at a time and the tracks are confounding. However, by the time they get further north they move much more predictably and you are only tracking one storm. No, you can never plot a land fall, because they tend to skip along the coast, but you can generally plot the arrival time well. On a coastal trip, that is enough to get tied up and into a motel. One one of my trips we did adjust and hurry back in front of a tropical storm, but it only made for fast sailing. We could just as easily have waited 2 days, but the Bay is so full of hidey holes, we figured we would chose one if things got too testy.
Simply be conservative with the weather; never wait too long to seek shelter.