Pilots Association president William Rowe Boutwell instructed the designers to model the vessel after the America's Cup competitors of the day.

Although steamboats were readily available at the time, Virginia was built with no engines so as to maintain the pilots' sailing skills and train new apprentices.

Following the war, she was fitted with two 75 hp diesel engines, which necessitated a shortening of her fore boom to accommodate a smokestack.

[6] She is a gaff rigged knockabout schooner, meaning she lacks a bowsprit; her headsails can be handled and furled from the deck.

The Virginia Maritime Heritage Foundation's sail-training programme was proving unsustainable, it costing about $1 million a year to run the schooner.