Winslow Homer’s artistic journey carried him from a widely admired illustrator to one of the most influential painters in American art. Beginning with works such as Sharpshooter on Picket Duty (1863, Portland Museum of Art) and extending to late masterpieces like Driftwood (1909, MFA Boston), Homer continually reinvented his approach and deepened his vision. Originally sent by Harper’s Weekly to document the Civil War, he focused on the human dimensions of conflict rather than battlefield heroics. In the 1870s he began to explore watercolor, a medium that opened new expressive possibilities, and he traveled to England to further refine his technique. After establishing a studio at Prout’s Neck, Maine, Homer turned his attention to the elemental struggle between people and the natural world, producing the dramatic seascapes for which he is now renowned. Seeking relief from Maine’s severe winters, he also traveled repeatedly to the Bahamas, Cuba, and Florida from the mid-1880s onward, creating luminous watercolors that capture tropical light, color, and daily life. Homer’s career was a sustained effort to portray the American experience and the natural world with clarity, honesty, and innovation—an effort that secured his place as a cornerstone of American art. Together, we will trace this remarkable evolution, with optional visits to local museums and to Homer’s studio at Prout’s Neck, Maine.