As any good sailor knows, you can't navigate a sailboat by way of Google Maps. Here's an excerpt of the appropriate NOAA chart showing the anchorage in more detail:
As you can see, one of the islands shown on Google isn't really there anymore. Ironically, the now-missing island is called "High Island". Typically, we will anchor to the southeast of Big Island; there is usually plenty of room, the water is deep, and the bottom is relatively easy to anchor in. Be cautious when navigating into or out of the area though; the bottom here is prone to shifting and if you stray out of the channel you're likely to get grounded. Fortunately though, the bottom is relatively soft and getting yourself unstuck is possible. (Yes, I'm speaking from experience)
I've been here numerous occasions with Ryan, sometimes to spend the afternoon, sometimes to spend the night, and it's always fun. Often times after staying the night, however, one or more of the folks aboard will be, shall we say, a bit under the weather due to the previous nights revelry. As such, we started affectionately referring to this spot as Hangover Cove.
Part of what makes Hangover Cove a good place to anchor is the presence of Flat Island, which is a small, mostly wooded island that has a few paths hacked through the trees and a tiny spit of a beach that is perfect for landing a dinghy on. If you don't feel like cooking on the boat, or are just looking for an excuse to launch your dinghy, a trip to Flat Island is most certainly in order. Given the opportunity for hilarity on dinghy rides, and since Flat Island is such a nondescript name, we've taken to calling it Shenanigans Island.
So if you're sailing in the Chesapeake just south of Annapolis and are looking for a good spot to anchor for a rest or a meal, find the Rhode River and give Hangover Cove a go.