Dr. Alexander Hamilton was a Scottish-born doctor and writer who lived and worked in Annapolis in 18th-century colonial Maryland. Historian Leo Lemay says his 1744 travel diary Gentleman's Progress: The Itinerarium of Dr. Alexander Hamilton is "the best single portrait of men and manners, of rural and urban life, of the wide range of society and scenery in colonial America." His diary covered Maryland to Maine; and biographer Elaine Breslaw says he encountered: "the relatively primitive social milieu of the New World. He faced unfamiliar and challenging social institutions: the labor system that relied on black slaves, extraordinarily fluid social statuses, distasteful business methods, unpleasant conversational quirks, as well as variant habits of dress, food, and drink."

Annapolis is the capital of the state of Maryland. It is the county seat of Anne Arundel County and its only incorporated city. Situated on the Chesapeake Bay at the mouth of the Severn River, 25 miles (40 km) south of Baltimore and about 30 miles (50 km) east of Washington, D.C., Annapolis forms part of the Baltimore–Washington metropolitan area. The 2020 census recorded its population as 40,812, an increase of 6.3% since 2010.