If you set the hook in the outer anchorage (Miles River; the inner bight will likely be full) the water taxi will come get you. Other nearby anchorages
are across the river (Leeds Creek, etc.). You can use ActiveCaptain chart mode to get a feel for location, even if not perfect for distance calculation and so forth. There's a dinghy dock
in between The Crab Claw
restaurant and the Patriot tour boat. Another I've heard of at the head
of the creek, near Foxy's Grill
; haven't seen that in use...
If you DO anchor
out there, take pains to honor the scope
that others before you have determined, but then take more pains to set the hook big time.... since many of the folks who beat you there will have decided that zero scope
is fine. If it's quiet, it's a nice anchorage; if it gets blowy, it's still usually OK but you'll be glad you anchor is buried.
San Domingo Creek is a good St. Michaels anchorage, and there's a dinghy landing at a small park on that side of town, but the distance might be too much for you... since you have to go through Knapp's Narrows to get there. And then back up the Bay and up Eastern Bay to get to the Wye. Could be nice sailing, though... if you have any wind