Next time you're heading South, drop me a line, we'll have a mini-Tartan rendevous....I'm on the lower Potomac (AKA washing machine
You can't pass up Onancock next go-around, there's a nice "old-time" feel about it and it has a few decent restaurants. Tangier is a good thing to do at least once, great cultural experience. Beware of the currents as you tie up to Parks Marina, they whip thru at 4-5 knots.
If you make it further down the bay, Kiptopeke State Park is really a cool place to anchor, but only if the weather is benign. You anchor in behind the concrete ships in about 15-20 feet of water in a nice sandy bottom and fish for flounder or cobia later in the year. There's hiking trails, beaches, hot showers on shore and ice cream in the little convience store run by the park.
Cape Charles is two-sided. There's the city harbor and marina that is cheap and convenient, but not much to look at and you have to walk across the railroad tracks to get to the restaurants. Then there's the new fancy Bay Creek marina on Kings Creek, but I've never ventured into it (I'm told that there's a lot of shoaling)
Anyway, the Bay is a wonderful place to explore and it could take a lifetime to see it all, Happy Sails