I also notice that the schedule made no sense; I think the first reference to Hampton Roads actually meant Lewis, DE, or perhaps Cape May, NJ.
I've done the trip many times, and there's a bunch of stuff about it on my blog:
Sail Delmarva: Search results for circumnavigation
I'm not much of a rally person. I would rather be able to stop where and when I want, for as long as I want. I think it is also safer to go alone, because you are not pressed by a schedule to sail when you would rather not.
The first time I went I had a 1200-pound boat and a 9-year old for crew. We had a towable for a tender (the boat only drew 12 inches) and my off-shore expereince was limited to a beach catamaran. But it was safe because we picked our weather. We also made a lot more than 3 stops--9, I believe--and those stops were highlights. Of course, some of the stops would not accomodate a rally group--too big--which suited us even better.