After moving to New York City in 1899, Marsden Hartley visited the famous poet Walt Whitman, a kindred spirit who often encoded his gay identity within his poetry through a mystical experience of the visible world. Hartley similarly believed that an artist’s subject matter represented a form of self-portraiture, and often used his paintings as vehicles for his own same-sex desires, which he subsumed within a spiritual sensibility.

In the winter of 1916–1917, Hartley traveled to Bermuda, where he was joined by the artist Charles Demuth. "A Bermuda Window in a Semi-Tropic Character" recalls Paul Cézanne’s tabletop still lifes and similar vibrantly colored window paintings by Henri Matisse. However, Hartley’s view onto a bay also includes coded male symbolism in the phallic cloud and fruit, as well as the erect flower. His pairings—of walls, curtains, tiebacks, pears, plums, sails, and leaves—are suggestive symbols for couples and coupling that set the stage for the single flowering blossom.