This tour explores the diverse collection of buildings, memorials, and monuments located in Washington’s historic commercial core. Downtown Washington is a large area stretching west from Judiciary Square to Farragut Square and Foggy Bottom, and north to Massachusetts Avenue NW and Dupont Circle. It is not necessarily a clearly defined area, and Washingtonians may have differing opinions on where Downtown's edges are. Regardless, Downtown is known for its historic sites (most notably, the White House), office buildings, hotels, restaurants, entertainment and sports venues, and parks.

The historic core of Downtown is located east of the White House and north of Pennsylvania Avenue — rather than along K Street and Connecticut Avenue NW, where many office buildings were constructed in the postwar years. Historic Downtown lies at the heart of the federal city, as laid out in 1791 by the French engineer and planner Pierre L’Enfant. This area is traversed by Pennsylvania Avenue and 7th Street NW, which have been important transportation routes since Washington's beginnings. Pennsylvania Avenue, between the city's two most important points, Capitol Hill and the White House, quickly became a thriving thoroughfare. This stretch of Pennsylvania Avenue is especially significant, as every four years it is the focal point of the presidential inauguration route. 7th Street became an important commercial corridor thanks to the north-south thoroughfare's connection to points north of the city, both in the District and in Maryland.

F Street also became an important center of commerce and entertainment, and some of the city's oldest and most architecturally significant buildings, designed in a Greek Revival/Neoclassical style, can be found along and near this street: the Old Patent Office, General Post Office, and U.S. Treasury Building. Next to these government buildings are clusters of smaller, historic commercial and residential buildings designed in various styles that were popular in the years right before and following the Civil War. In addition to these smaller buildings are some of the city's early "skyscrapers" dating to the 1880s and 1890s, such as the Atlantic and Sun buildings, and the Washington Loan & Trust Company. Over the years, many historic buildings (and facades) have been incorporated into new construction, giving the neighborhood layers of history that are quite visible to pedestrians. Chinatown, centered along H Street, adds additional character to Historic Downtown, with its specific design elements. This particular Chinatown dates to the 1930s, as the community was forced to move from the Judiciary Square-Federal Triangle area to accommodate new federal office building construction. The buildings, many of which predate the 1930s, were repurposed and altered by the Chinese American community, with the 1843 Mary Surratt House as a prime example of new uses and layers of history.

It is important to note that only a portion of this area falls within the Downtown Historic District, which is generally centered along 7th Street and F Street, east of 11th Street, as well as the Financial Historic District along 15th Street. Nonetheless, there are many historic landmarks that fall within and outside the historic districts' boundaries.