If you want to catch some zzzz's any closer to the water in this 17th-century port town, you'll have to spend the night on a boat. The Marriott is right at the edge of the Chesapeake Bay, a short stroll to the Naval Academy, state capitol, and historic district.
The formality of the marble entry is offset by an adjacent space that houses model ships and photos of Annapolis from the 1800s, a great primer before exploring town. Most of the 150 traditionally furnished guest rooms have city or water views; 16 have waterfront balconies with vistas of the bay and Bay Bridge.
If you arrive by boat, you can tie up to Pusser's Landing, the hotel's open-air restaurant that doubles as a dock. An offshoot of the Virgin Islands' Pusser's Rum Company, its Caribbean-inspired menu spices up Chesapeake favorites with a dash of ginger or rum. When foul weather rolls in, snuggle up in Pusser's indoor publike alternative.
Bottom line: A one-stop destination for everything Annapolis offers–history, good seafood, and the mighty Chesapeake.
Annapolis Marriott Waterfront Hotel, 800-336-0072; annapolismarriott.com. Rooms for two from $279; waterfront from $339 weekdays, $429 weekend. Packages that include a two-hour sail on a 74-foot schooner from $339.