Wachapreague is a neat place, and many years ago it had a great restaurant. I haven't been there is a while, but from what I recall about the inlet, there was two entrances, the deepest of which was a cut along the shore that connected with the main inlet. The main inlet entrance, which is well marked, was nothing more than a slot through the surf. I was real hairy when the tide was ripping out and there was an easterly wind.
Sand Shoal Inlet is an easy passage, lots of deep water inside the inlet that is well protected and provides great anchorages. Excellent flounder fishing just inside the inlet and along the channel edges.
The only other inlet that's sailboat navigable is Great Machapongo Inlet, which is situated between Wachapreague and Sand Shoal inlets. The inlet is deep, with the exception of the seaward end where it shoals up to just 8 feet. Once into the inlet you'll find depths to 50 feet and a ripping current during during tidal changes.Consequently, this is one of those places where you can only access the back bay anchorage areas during slack tide. The only town here is Willis Wharf, which is a small fishing village.