Chesapeake Bay
Is a treasure. Unfortunately, finding seclusion can be a chore. Fortunately, you have two weeks and most of the "best" places may only fill up on good weather weekends, so take advantage of getting to the best places during the week. If you are starting out in the upper bay, put a hook out behind the Coast Guard station at Still Pond. A few miles south, head into Rock Hall and anchor in Swan Creek. Then go explore the upper reaches of the Chester River. Lots of fairly secluded places all along the upper shore there. If you have courage and shallow draft, head back down the Chester and go thru Kent Narrows and into Prospect and Eastern Bay. Head down the Miles River and into the Wye River. Don't stop at Shaw Bay as everyone does. Keep going up the Wye and head into Dividing or Granary Creeks on the north side of the river. The next day head down the Miles River into St Michaels and eat crabs at the Crab Claw. Take a transient slip and explore the town. The next day, head back up the Miles, into Eastern Bay, go across the Bay to Galesville or lunch. Then head up the Rhode River for the night. This is a quick and dirty, but it's a start. You'll love the bay and I hope you have wind.