We have done the circumnavigation route a couple of times. You should note that the only really passable inlet from Cape May/ Lewis to the entrance to the Chesapeake at Norfolk is Ocean City Maryland. Though passable, this is also not a very nice inlet in many different types of weather and tides. certainly not the place for a first timer in many ways.
I would suggest if you want off shore experience a different tack. Go to Cape May and take a few days from there. 26 miles to Atlantic City, 16 miles to Lewis across my favorite...Delaware Bay. You would get some ocean experience this way. Also Cape May, Atlantic City are two of the very best NJ inlets and along with Manequan are the only ones that don't have issues associated with them.
PDAltair, I remember your blog/story about your trip and it was quite memorable. Your catamaran is a lot safer going in some of the inlets I would not try with a keel boat.
Regarding small boats, you do need to be careful, but with careful planning it's safe. Try to get a copy of "Eastern Shore, Western Wind", a classic tale by DeGast, I think. Even if you don't do the trip, it's great read. He did the trip in a Sailmaster 22, I recall, taking 3 weeks and stopping everywhere.
Regarding Delmarva entrances, we once did a trip in the wake of a Hurricane, with an 8 foot swell running; the only entrance that was not breaking was Chincoteague. OC was closed. Chincoteague was casual and is a much easier entrance in a swell, in my opinion and expereince, than OC. OC is simply more popular as it is better known, has more marinas, and the piloting is simpler. Remember, the Coast Guard HQ for the eastern shore is in Chincoteague and there is a commercial trawler fleet there. Big boats that draw 10-12 feet (they do have to watch the tide). If you get sloppy, you may see 7 feet at low tide, but a boat drawing 5 feet would be very safe, and I have seen larger boats in there. However, Chincoteague is not well lit and should be avoided at night unless you know the route.
There real challenge in Chincoteage is dockage. Trailer boats should be able to find many slots, but multihulls and deep draft boats can only go a few places (town dock, Chincoteague Inn)
Watchapreage is also cake in a trailer boat, as long as there is no big on-shore swell (it is reasonably protected in moderate north and south wind by flanking bars). The bar is about 7 feet and the channel is dead straight. Good for power boats and shoal draft boats only.
Other inlets are not for the feint hearted, are only for fair weather, and shoal draft boats.