DAY 1 From D.C., take a 1 1/2-hour drive southeast to Flag Ponds Nature Park (410/586-1477; www.calvertparks.org; open weekends only), between St. Leonard and Lusby, Maryland. It's a 20-minute trip from there to Solomons Island. Rent a boat from Solomons Boat Rental (800/535-2628; www.boat-rent.net) and tool around on the Patuxent River. Stay at Comfort Inn Beacon Marina (255 Lore Rd.; 800/424-6423; www.comfortinn.com; doubles from $89) or a B&B (www.ecalvert.com/guide/bb.htm).
DAY 2 Follow Route 2-4 north to Route 50/Bay Bridge; turn onto 322, then continue to St. Michaels. Two hours will get you there, in time for lunch at the Crab Claw Restaurant (Navy Point, off Rte. 33 W.; 410/745-2900; lunch for four $45) and a stop at the Chesapeake Bay Maritime Museum (Mill St., Navy Point; 410/745-2916; www.cbmm.org). Drive 10 minutes to Tilghman Island and climb aboard the skipjack Rebecca T. Ruark at sunset (410/829-3976; www.skipjack.org).
DAY 3 Take the back roads for the 100-mile trip to Ocean City: Route 33 East to Route 333; from there, board the seven-minute car ferry across the Tred Avon River, then follow Route 331, which becomes 318. At Federalsburg, get on Route 313 South to the Delaware border. Take Route 24 East to Highway 113 South. Follow 113 to Highway 90 East. Ocean City is not known for great accommodations, but the 1920's Lankford Hotel (807 Boardwalk; 800/282-9709; www.lankfordhotel.com; two-room suites from $107) is fun.
DAY 4 Enjoy a morning bike ride along the Ocean City Boardwalk (bicycles are allowed until 10 a.m.; there are rental shops galore). Then, drive 20 minutes south on Route 611 to Assateague Island National Seashore. Neighboring Chincoteague is also worth a visit.
DAY 5 Head west for one hour to Crisfield and a great crab-cake sandwich at the Waterman's Inn (901 W. Main St.; 410/968-2119; lunch for four $50). At the boat landing about two blocks away, hop on the Captain Jason II for a 40-minute cruise to Smith Island.
Don't miss Jessie Hartland's new children's book, Clementine In the City, about an adventurous poodle who becomes a travel writer. It's out June from the Penguin Young Readers Group.