Between the St. Marys River and Pt. Lookout there are only a few destinations available to deep draft the sailboats.  Most of these are on Smith Creek.  Boats drawing less than 6' used to be able to get into the entrance to Lake Canoy, just above Pt. Lookout.  I anchored there on Vela Llena back in the late-1970s, but haven't been back since.  I can't recommend it as beautiful anchorage.  The channel is used by a large number of small power boats, primarily fishing boats, as there was a public ramp on Lake Canoy.  Assuming the channel is still accessible, I would only recommend this destination as an temporary anchorage when protection from northerly winds and quick access to the bay are essential.

Smith Creek offers a number of quality anchorages plus several large marinas.