The area south of the James River, sometimes called the Southern Tidewater, includes the cities of Chesapeake and Suffolk and the counties of Isle of Wight, Southampton, Surry, and Prince George. The cities of Chesapeake and Suffolk are really municipal counties covering large land areas. The City of Chesapeake, formed in 1963, takes in the former Norfolk County and city of South Norfolk. The City of Suffolk, created in 1974, takes in the former Nansemond County.

The terrain is very flat and is drained by many rivers, lakes, and inlets. Part of both Suffolk and Chesapeake are covered by the Great Dismal Swamp, 200,000 acres of forested peat, a western portion of which in 1974 became the 107,000-acre Great Dismal Swamp National Wildlife Refuge. The English settled the area early. Some of Virginia's most important and venerable buildings of the seventeenth century are here, including Bacon's Castle and St. Luke's Church. By the late eighteenth and the nineteenth century, the soil was exhausted, and many families left. In the late nineteenth century new crops and enterprises appeared: peanuts, timber, and pig farming. Along the James at Hopewell, another industry, munitions, became a staple in the early twentieth century. This development has led to some rejuvenation, but great portions of the area remain rural and agricultural. They retain an air of time passed by. At the east, extensive suburban development, a spillover from Virginia Beach, is taking place in Chesapeake.