Born into a wealthy and political family in Albany, New York, the American surrealist artist and poet Kay Sage moved to Europe as a child with her mother. After living in Rome for over a decade, she moved to Paris in 1937, where she encountered and was deeply inspired by European surrealism. Following the outbreak of World War II, she and her future husband Yves Tanguy emigrated to the United States, settling on a farm in Woodbury, Connecticut.

"Starlings, Caravans" is emblematic of Sage’s psychologically charged compositions that merge architecture and landscape, and are meticulously rendered with an almost photographic precision. A strange, boatlike structure with exposed ribbing appears tilted on its side in a barren gray landscape suggestive of a vast sea or desert. The composition’s enigmatic subject matter and sense of eerie desolation reveal the influence of the Italian metaphysical painter Giorgio de Chirico, whose work Sage greatly admired.