This depicts Virginia leaving a Maine cove in October 1608 and heading into the Atlantic for her voyage to England. Virginia is in full ocean rigging but the square mail sail is shown furled on its yard. This will soon be deployed in place of the sprit main. This is the same sail configuration as the 1/10 scale model in the Jane Steven Visitor Center.

The painting was originally done with white sails and a black chevron design on the bulwarks. The tanbark sails would most likely have been used in the 17th century as this treatment prevented mold on the sails. Most ships of the period were painted in bold colors and patterns so that they would be recognized from a distance. The black and white chevrons in the original painting are Tudor colors of Queen Elizabeth I. The red and white chevrons are the colors of King James I and the Stuarts. The color changes were done digitally.