The Chesapeake Bay is the largest estuary in the United States and is home to numerous small islands. Many of these have already vanished, and those remaining are continuing to lose ground. Over a few decades several of these small places were abandoned as the waters started to roll over the lands around the mid-nineteenth century. Houses were torn down, while some people moved within or to other islands and others migrated to solid ground when other measures failed to secure the small islands. Some people left earlier than others, but there were moments when it became difficult to retain the society of the islands. By telling the story of the Chesapeake Islands, this paper outlines the reactions of individuals and society to changes in their living environment. The aim of the article is thereby to explore the variables influencing human thresholds to migration in times of changing environments. Societal factors, as well as natural stimuli, are explored that led to migration at a certain time and place. By drawing attention to the sinking islands in the Chesapeake, I advocate the consideration of examples from the Western Hemisphere in debates on island loss and migration.