Tilghman Island is 50 miles from Annapolis, 80 miles from Washington, DC. It is 50 years from today's date. Expect to find a locale with more in common with the coast of Maine than the Nation's Capital. Put in at Dogwood Harbor just about a half mile south of the Knapp Narrows drawbridge. Free parking and secure. You may then circumnavigate the island which is about a 7-8 mile paddle or go North and out through the Knapp Narrows under that same drawbridge, then head Northwest to Coaches Island. You'll find a beautiful beach, very warm water in the summer, and the beauty of the Chesapeake Bay. When you get your boats loaded for the trip home stop at the restaurants on either side of the drawbridge for some crabs and beer. For a nice overnight - stay at one of the bed and breakfasts in St. Michaels just 10 miles up the road. No finer place in the US.
St. Michaels, MD is a beautiful colonial seaside town on the Chesapeake Bay. Many, many restaurants, gift shops, antiques, and B&Bs. Tighlman is much quiter but the Tighlman Island Inn is very nice to stay or just a meal - you'll have a great view of the Bay.
Sign says there is a daily parking fee but I don't know where you pay and never have. Be happy to if there was someplace to do it.
Route 50 East from the Washington Beltway 20 miles to the Chesapeake Bay Bridge. Over the bridge (this is a big one, 4 miles). In Easton take route 33 West/South through St. Michaels and finally across the Knapp Narrows drawbridge. Dogwood Harbor is on your left 1/2 mile from the bridge. Park along the grass side, not next to the boats - these are mostly working boats and they need access.
Tighlman Island/Dogwood Harbor is one of the last places you'll find working Skipjacks - sailing ships that harvest oysters from the Bay. No prettier boat in my view. Books on the Chesapeake Bay will certainly cover this.