I've been spending time looking at charts and google earth for possible anchorages on this upcoming trip. The cool thing about Chesapeake Bay, as you can see from the satellite image below, is that there seem to be anchorage everywhere. It is not a matter of finding an anchorage, it's a matter of finding one that you like best.
The northern most point of the trip will be Oxford, Md. I would like to tie up there midday to resupply and maybe get a sandwich at the store in town. But I don't want to overnight there, I'll head off to one of the nearby rivers or creeks. The one that looks good to me right now is Latrappe Creek, about eight miles from Oxford.
Here is a detail shot of the lower part of LaTrappe Creek. I can't even begin to count the possible anchorage there. Wouldn't it be nice to spend the evening tucked in behind that quarter mile long sand spit right at the mouth of the river?
And below is the lower portion of Smith Island with town of Tylerton at the top center. Just like Oxford, I want to visit Tylerton but not overnight there. But you can see there are plenty of anchorages, some marked with X's, within a short sail of Tylerton.
I kind of see this trip as an extended walkabout. I've got a few places in mind that I want to visit - Oxford, Smith Island, the Hooper Islands and maybe Tangier Island. But I don't have specific goals for each day of sailing. I'll just look at the wind and go with the flow.