Broad Creek to St. Michaels, MD
Sailors from Annapolis and points further north on the Chesapeake might wonder why I would include St. Michaels in the section on the Choptank River.  After all St. Michaels is on the Miles River, not the Choptank or any of its tributaries.  Well, that's not quite true, the St. Michaels harbor may be on the Miles, but the "Backdoor" to St. Michaels is on San Domingo Creek, which is connected to Broad Creek, which is off the Choptank.  Sailors from south of Annapolis generally go to St. Michaels through the "Backdoor" and avoid the crowded anchorages and the charter fleet in the harbor.  It is also a much shorter distance from my home port on the Patuxent River to the "Backdoor" than to the harbor.
Broad Creek offers two primary anchorages to deep draft vessels, Leadenham Creek and San Domingo Creek.  Boats that draw 7' or more will find Leadenham Creek more hospitable of the two.  Both offer plenty of protection and the best access to the town of St. Michaels at the head of San Domingo Creek.
There are many other coves and creeks off Broad Creek that could be viable anchorages, but I have not personally explored any of them.
The light off Nelson Pt., which marks the entrance to Broad Creek, is hard to pick up during daylight if you are approaching from the south.  The mark faces east-west and is easier to see during the daylight when approaching from either of these directions.  This mark must be correctly identified as it defines the limits of the long shoal that stretches south and east from Nelson Pt.  Once you have cleared this mark, the channel heads NW to clear the opposing shoal that stretches from the eastern shore of the creek.  Once you have crossed this second shoal, the creek is wide and deep all the way to where is splits into Leadenham, Bozman, and San Domingo Creeks.
The entrance into Leadenham Creek is well marked.  The best anchorage is in the first cove on the right as you enter.  Give the point of land between Leadenham Creek and Bozman Creek a wide berth as a shoal extends well south of the point.
San Domingo Creek is well marked, but any boats drawing more than 6' should stay close to center channel and watch their depth sounder all the way in.  The cove on the right has plenty of water and offers great protection when the wind is strong out of the north or south.
My old sailboat, Vela Llena, at anchor and rafted with Emp;athy in Leadenham Creek off Broad Creek. Click on picture to view at full resolution
Vela Llena and Empathy
Photo by Gene Limerick