This book explores the influence of classical texts upon early European settlers and inhabitants of the Tidewater region of Virginia, addressing how Greek and Roman literature and culture shaped and sometimes challenged prevailing assumptions about personhood, liberty, town planning, and representative government in Virginia during the period of its expansion from the fort at Jamestown to Thomas Jefferson's Virginia. Benjamin Stephen Haller introduces the reader to the Ovid translation which George Sandys penned during his time in Virginia as Treasurer; William Strachey's account of the wreck of the Sea Venture, likely one inspiration for William Shakespeare's The Tempest; William Byrd II's writings, including his secret diaries which record the intimate details of the life of an Indian Trader and plantation owner in the early eighteenth century; and Jefferson's expansive Enlightenment Era appetite for knowledge classical and modern. Haller's analysis of these texts is carefully anchored in a discussion of the cultural historical context of the Grand Tour, the excavations of Pompeii, the eighteenth-century mania for Palladian architecture, the construction of the campus of the University of Virginia, and new Enlightenment ideals of personal liberty and human rights which came to the fore during Jefferson's lifetime, and which he helped to enshrine in modern American political thought.