Homeward Bound suggests both in its title and composition an adventure whose safe conclusion is almost at hand. Its theme closely parallels those of romantic and symbolist artists and writers of the nineteenth century, such as Delacroix, Redon, and Poe.
Fresh and direct in technique, optimistic and almost joyful in mood, this painting has been deemed one of the best and most representative Ryder marines of the 1890s. It was painted as a gift for John Robinson, an English artist and sea captain on whose ship Ryder traveled abroad. The serene mood of Homeward Bound seems to reflect Ryder's enduring friendship with Captain Robinson, whom he had known since 1883.
Though small in scale, Homeward Bound represents a fusion of pictorial and thematic elements because of the focus on a lone boat: a sailing vessel with two figures. The upward tilt of the sail gives the image its buoyancy; placed directly in the center of the canvas, it breaks the otherwise continuous horizon line and seems to anchor the composition. The bright line of sun backlighting the cloud at the center right gives a directional push to the composition, further suggesting that the wind and water are propelling the boat toward the still invisible land. In Homeward Bound, Ryder brushed on unblended paint in thin, scumbled layers, capturing the sea in a greenish light and showing a brisk wind that breaks the surface of the water into foaming crests and the sky into strata of coursing clouds. The artist use pink highlights in the sky, an unusual tone that suggests an ebbing light. Homeward Bound displays a heightened realism, attesting to Ryder's fascination with and careful observation of the sea.
Duncan Phillips appreciated both the realism and broader symbolic meaning of this painting. He wrote that "[a]ll of Ryder is in the small marine entitled Homeward Bound....[T]hat little boat at the center of the composition as each of us is at the center of his particular universe, symbolized the soul's adventure as it traverses the vast, uncharted solitude, traveling toward the unknown."