With 17 days you probably have enough time. I remember when Art did the trip he really enjoyed it, but at the same time it seemed like there was a lot of travel time. They also ended up having to alter plans because of an early season hurricane.
I've been wanting to do the trip myself but on the other hand I normally go down to the Annapolis boat show every year and stay a couple extra days and have driven around a lot of the area. After doing this a few times my impression is that the cruising grounds we have east of us (Newport, Martha's Vineyard, Essex, Cuttyhunk, Block, etc) are actually nicer than the Chesapeake in addition to being easier to get to. Maybe if I was there by boat I'd change my mind, and it is something different, but having visited a lot of the cruising stops by car (Annapolis, Baltimore Inner Harbor, St Michaels, etc) I'm not as eager to head that way instead of going east as I was in the past.
What's the furthest east you've gone? Have you been past Newport?