The most popular town on the Eastern Shore, St. Michaels has a beautiful harbor with several waterfront dining options, the
Chesapeake Bay Maritime Museum, and Talbot Street, studded with more restaurants and boutiques, and a classic ice-cream shop.
Where to stay: The Inn at Perry Cabin, 308 Watkins Ln.; 866/278-9601 or perrycabin.com. Five Gables Inn & Spa, 209 N. Talbot St.; 410/745-0100 or fivegables.com.