If I were going to make the Delmarva Loop, and headed south in Chesapeake Bay there are a couple places near Cape Charles, VA that boats with a relatively shallow draft (under 5-feet) may wish to consider. Bay Creek Marina, formally known as Kings Creek Marina, has really improved over the years. It has been quite a while since I last visited this place, but it's on my bucket list for the upcoming season. Bay Creek Marina - Virginia Is For Lovers
There is some dockage near the Coast Guard station in Cape Charles Harbor, but the last time I checked it was very limited. There are some new restaurants in Cape Charles too, including Bahama Breeze, a chain that serves excellent cuisine. It's a neat town to visit, lots of old, historic buildings that have been restored, but like any town on the Chesapeake's eastern shore, it is surrounded by tidal marsh. When the sun goes down, the skeeters take over.
If you don't really need dockage, then I would just drop the anchor in the sheltered waters behind the concrete Liberty Ships at Kiptopeke Landing. The area is protected from most westerly winds and there's a great state park to visit. Miles of picturesque beaches to explore and let the kids collect shells of all kinds.