In Voyage 5 of Chesapeake, Rosalind Janney, so called after Shakespeare's "fair Rosalind" in Twelfth Night," is introduced to the reader. Unfortunately, she does not have the looks of the Rosalind after whom she is named and is all too aware of the "curse," especially for a girl as her mother points out. She is 26 years old when she leaves the home she loves, determined to do so in "good spirits" even though it is not how she feels. She waits for "everything to fall into place" and, when it doesn't she wishes her younger sisters well in their choice of suitors. Whilst reading Twelfth Night, which she had previously though ridiculous, she is suddenly inspired by Roaslind's words and becomes a good manager on her father's homestead and has a natural ability to manage the slaves. She discovers that her father has been trying to find her a husband, even offering a size-able portion of his land to any suitor but Rosalind remains unmarried. She finds it an "upside-down world" and dismisses her father's romantic view of a satisfied woman when she considers her own sister's hapless existence. 

Rosalind wonders why her family ignore some of their ancestors in favor of a rather far-fetched story of "cavaliers," her father insisting that Simon Janney, who embarrassed the family, is not the one to be remembered. Although Rosalind has asked her father to stop "peddling me through the countryside," he eventually finds her a husband but she must relocate across the water to Maryland a place "only slightly less formidable than death." Her future husband is also Catholic but he has promised that Rosalind does not have to convert.

Thus she sets off on her journey in September 1701 with a ship and slaves- the "dowry of a princess." When she sees Hugh Steed and his lovely daughter, Evelyn, she feels the full extent of her own shortcomings and wonders if she will be able to go through with the marriage. She is reminded of her father's words, that she is "granddaughter of a Cavalier," and promises herself that she will be brave.