Four boys perch on the high side of a steeply heeling catboat buffeted by choppy bottle-green water. The boat’s home port, Gloucester, is lettered on the stern. Winslow Homer painted Breezing Up in a postwar period during which many Americans longed for representations of a more innocent time. The painting enjoyed immediate popularity when exhibited in the country’s centennial year of 1876. Homer would turn increasingly to painting sea and seaside scenes, especially around Gloucester, Massachusetts.