The Historic Inns comprise three different boutique guesthouses, each set in a heritage building in the heart of old Annapolis: the Maryland Inn, the Governor Calvert House and the Robert Johnson House. Common areas are packed with period details, and the best rooms boast antiques, fireplaces and attractive views (the cheapest can be small). Check in at Governor Calvert House.
Don't miss a drink from longtime bartender Peanut at the Drummer's Lot Pub (5:30pm to midnight Tuesday to Saturday) in the Maryland Inn. Near the state capitol and a favorite of politicians over the decades, the pub dates back to 1772. They say Ben Franklin and John Adams shared a beer here.
Valet parking is $25 per night. Otherwise, try street parking or one of the nearby garages.