The largest estuary in North America, Chesapeake Bay is at once a playground for sailors, a destination for oyster slurping gourmets, and the home of towns and villages that date back to the colonial era. A good starting point is Annapolis, Maryland’s state capital, and briefly, from 1783 to 1784, the capital of the United States. The entire downtown is a historic district with its original town plan from 1695 and 120 18th-century buildings lovingly maintained. After walking the streets of Annapolis and charming Eastern Shore towns like Oxford and Easton, you should also make sure to leave time to actually get out on the water, either aboard a yacht or kayaking. Before heading back to EVEN Hotel Rockville order the Bay’s most famous dish, blue crabs served with butter and Old Bay Seasoning, at a waterfront crab house.