There are many places to stay near the heart of Annapolis, as well as at area B&Bs and chain motels a few miles outside town. A unique "Crabtown" option is Boat & Breakfasts, in which you sleep, eat, and cruise on a yacht or schooner; book ahead. Hotel reservations are necessary, even a year in advance, during the sailboat and powerboat shows in spring and fall and at Naval Academy commencement in May. Like most places on the water, prices are lower in the cooler months. You can save money on a hotel by booking a room away from the City Dock. To avoid relying on your car (and dealing with the limited parking in the historic area) ask if your hotel has a free shuttle service. More »