Your one week time frame and your desire to stop at interesting places don't go hand in hand. Some of the most interesting towns and anchorages are up rivers and creeks. Just getting from Severna Park to St. Michaels could take 8+ hours with the kind of light winds we get around here in the summer.
If you want to cover a lot of distance, that's great, but I think you'd have to go more into passagemaking mode, sailing round the clock with crew on watches, stopping only occasionally and not staying long any one place. That kind of thing can be brutal in heat and light wind.
You'd get to see more (though cover less distance) doing a "gunkholing" type cruise, sailing only by day and stopping every night in a different anchorage, but you might be surprised by how little distance you can cover in a week doing that. You'd be very lucky to make it below the MD line. The bay and its tributaries are enormous!
s/v Spindrift - TBD
formerly Lippincott 30 #41 (sold!)