Throughout an adult life that witnessed drastic cultural upheaval between the Civil War and World War I, Bertha Honoré Palmer (1849-1918) was continually called on to deploy her Victorian values in response to modern events. Being a woman only complicated this negotiation. But being a child of the American frontier granted her a latitude and mobility that were rare for women of her class and era – allowing her to challenge gender boundaries and occupy more than one cultural space at a time. Most of what has been written about Bertha Palmer’s life has been exceptionalist in approach and tone, ascribing her outsized social and political successes to her physical beauty and perfection of temperament. I believe Bertha Palmer’s importance as a crucial transitional bridge between True Woman and New Woman has been underestimated in this discourse. Near the end of her life, a move to Florida offered her the potential to resolve the inside/outside, domestic/public, feminine/masculine dialectics that lay at the heart of her restless movements. These contradictions and dichotomies that Bertha Palmer embodied on a grand scale do more to make her knowable to us today than the record of her words and actions can accomplish. Both her Victorian reticence and her modernistic construction of a seamless public façade have a way of hindering our best efforts to understand her motivations – especially the choice to move to Florida – despite a wealth of biographical material, including her correspondence housed in Chicago and Sarasota history centers, and contemporary news accounts. In the end, the cultural history of the Gilded Age gives us the only reliable lens for penetrating the veneer of Bertha Palmer.