Getting on the bay, or even a scenic chunk of shoreline, could be a challenge without prior planning. Public access is limited because much of the bay's shoreline is in private hands. So, for direct access to the water, you'll want to get acquainted with the many state and federal parks and refuges along Chesapeake shores or tributaries. Put in your own small craft or, far easier, rent one where you can. If you are looking for a charter and aren't sure where to find one, check local marinas.
Chances are, they'll know where the nearest charter boat docks.
Well, stinging nettles arrive in the estuary's saltier lower reaches during hot weather. Rainy springs seem to stave off the nettles, but this year has been awfully dry. Assuming you've visited Annapolis, and perhaps St. Michaels and Chestertown, here are five good answers. Each of the places I recommend will expose you to geographically and culturally distinct servings of the bay, or let you get out onto the water if you're so inclined. Some offer more tourism amenities than others, but none is so obscure that visitors will be stranded.