ON THE MENU IN ANNAPOLIS (AND ALMOST NO PLACE ELSE)
Steamed blue crabs from Chesapeake Bay. They're covered in Old Bay Seasoning. My favorite crab house is Mike's [3030 Riva Rd.; 410/956-2784; dinner for four $100], on the South River. You can sit on the deck, and the waiter will dump a big pile of crabs in the middle of the table. Anyone there can show you how to pick them apart. I think the best-tasting part is the back fin.
THE EASIEST WAY TO GET OUT ON THE WATER
Catch a water taxi [watermarkjourney.com] from City Dock. The taxi captains know all kinds of local stories—my father always says that when he retires from commercial real estate, he wants to be one of them. It's also cool to sail on the Woodwind [410/263-7837; schoonerwoodwind.com; $35 adults, $20 children, for a two-hour ride]. It's a wooden schooner that cruises the bay. Scenes from The Wedding Crashers were filmed on it.
BUT IF YOU REALLY WANT TO SAIL...
Charter a boat from South River Boat Rentals [410/956-9729; annapolisboatrental.com; half-day from $140; overnight $500] and drop anchor in Harness Creek, off the South River. It's good for swimming—just watch out for sea nettles—they sting. Dock for the night in St. Michaels. It doesn't take long to get there, but you feel really far away. —As told to Meeghan Truelove