This is where I live, a small (population less than 1,000) island in Chesapeake Bay called Tilghman Island. Or Tilghman's Island. Or just Tilghman.
It's at the southern tip of the Bay Hundred peninsula in Talbot County.
Some people (not me) refer to Talbot County as the Hamptons of the Chesapeake.
You can reach Tilghman in about two hours from either Washington or Baltimore.
Once here, you can eat crabs in warm weather and oysters in cold weather. You can fish. You can kayak. You can sail aboard the Rebecca T. Ruark, a 124-year-old skipjack (http://www.skipjack.org/). You can book passage on the Sharps Island, a former Swiftboat, for a tour of Chesapeake lighthouses (http://www.chesapeakelights.com/). You can keep an eye out for great blue herons, osprey, bald eagles, red fox, deer and wild turkeys. You can study painting with Walt Bartman of Glen Echo National Park; he has a studio here for workshops, usually in the warmer months. Check his web site http://www.yellowbarnstudio.com/classes.htm#Workshops to see if any are scheduled. Or you can sit beside Knapps Narrows (which separates the island from the mainland) and watch boats go back and forth. And watch the nation's busiest drawbridge go up and down.
The Tilghman Watermen's Museum (http://tilghmanmuseum.org/) can help you understand the island's history as a fishing, crabbing and oystering center. Phillips Wharf Environmental Center (http://www.pwec.org/) can help you understand today's threats to the health of the Chesapeake and to the watermen's way of life.
Two websites will help you find lodging, boat excursions and more: http://www.tilghmanmd.com/ and http://www.tilghmanisland.com/