Ships navigating into and out of the harbors around San Francisco in the late nineteenth century were typically met by a pilot, a local seaman familiar with the shallow waters around the coastline. After directing the ship through the waters, the pilot would return to his schooner and await the next ship. The pilot schooner Gracie S. traveled waters around San Francisco from the nineteenth to the early twentieth century, tirelessly aiding larger ships in their passage.

While working on this painting, artist Chris Blossom said, “I was really interested by the play of light on the sail against the dark blue sky, and by the contrast of the boat against the water.” The artist used the original plans for the ship Gracie S. as a reference, as well as shots of the shoreline around Alcatraz. The Pilot Schooner is a striking tribute to ocean, sky, and the labors of men.