Alexander, Charles, and William Fyffe of Dron were three brothers who emigrated from Dundee, Scotland, to America in the 1740s. Alexander Fyffe settled in Savannah, Georgia, as a merchant with the business Alexander Fyffe and Company. William Fyffe, a doctor and planter, had a plantation on the Black River, Georgetown, South Carolina. Charles Fyffe, also a doctor and planter, first settled in Norfolk, Virginia, and then moved to Georgetown, where he purchased a lot and built a house in 1763. The brothers in America maintained ties with their family in Scotland, including their father James Fyffe, sisters Elizabeth and Magdalen, and brother John, a merchant in Edinburgh. The family also corresponded with a cousin, David Fyffe of Drumgeith, who traveled to Jamaica.
When Alexander Fyffe died in 1766, his family had considerable difficulty in settling his estate and collecting the debts owed to him. Alexander's will listed his sisters Magdalen and Elizabeth Fyffe as executrices, but as they both lived in Scotland, his brothers Charles and William were appointed in their stead. Over the next several years, William and Charles struggled to ascertain the condition of the estate and the debts owed to Alexander. As a result of the difficulty of traveling to Savannah in person, they were dependent upon correspondence with Alexander's former business partners, whom William suspected of dishonesty.
William sent his young sons, James and Charles, back to his family in Scotland to be educated, entrusting them to the care of his father and sisters. He hoped that the change in climate would improve their poor health. Intending for Jamie to become a merchant, he arranged an apprenticeship for him with his uncle John to learn the retail business, and planned for him to return to South Carolina at the age of 21. William wrote that if "his Merit should recommend him as a Partner in a good House, or his Friends would support him with sufficient credit to commence Business...he could hardly fail with a common Share of Understanding & Industry to acquire an Easy Fortune in a Short Time." Of his younger son, he wrote," if Charly lives & has an Inclination to Physick cherish it, it has its advantages, its a genteel business no capital necessary" (1771 May 17).
In later years, William's medical practice declined and rice planting took more of his attention. He wrote to his sister, "indeed the number of doctors in this Town and my usual sickness in the Fall when we've most chance for business makes me find Physick less profitable than the labour of the few slaves I have in the field" (1771 November 15). In William's last letter to his sisters, he described his symptoms of growing paralysis and made final arrangements to conclude his business affairs. He ended, "My Blessing to my sons God grant them Health Virtue and Happiness. Adieu my dear Sisters since the Pleasure of meeting in this world is denied us that we may have a joyful meeting hereafter is the earnest Prayer of your most affectionate Brother, William Fyffe" (1771 December 1). After William's death, Charles continued his efforts to settle Alexander's estate on his sisters' behalf. Cousin David took on the responsibility of providing for William's sons in Scotland, who needed financial assistance to continue their education and become apprenticed. Plans were somewhat altered by the advent of the American Revolution. On September 25, 1775, David wrote to Elizabeth that Charles "desires that Jamie shall not go out to Carolina untill the disturbances & madness now reigning there are subsided, at present they are in the utmost confusion."
During the Revolutionary War, Charles Fyffe was in charge of a loyalist refugee hospital in Charleston. After the war, his estate was confiscated and auctioned off. He returned to South Carolina in 1784, but was living in New York by 1786.
In 1836, a descendant of David Fyffe of Drumgeith, also named David Fyffe, enlisted in the 46th, or South Devonshire, Regiment of Foot. He was the eldest son of Major David Fyffe of the 44th Regiment, whose family resided at the Lodge in Broughty Ferry, on the estate of Smithfield near Dundee. With his regiment, he embarked for Gibraltar in 1837, then sailed to Barbados in the British West Indies in 1842. David strongly disliked Barbados when he first arrived, calling it "hot, dull, stupid and unpleasant with hardly a redeeming quality" (1842 March 6). In 1843, he was transferred to the island of St. Vincent, which he described as "a beautiful island, all fine grand looking hills covered from top to bottom with rich, green, beautifully green wood" (1843 September 6). He also noted that "There are a tremendous lot of Scotch people in this island" (1844 April 3).
David Fyffe's time in the West Indies was punctuated by frequent appeals for leave to visit his family in Scotland, which were consistently denied. While in St. Vincent, he fell in love with and proposed to a young woman, Mary Cumming, but his parents refused permission and he was forced to break the engagement. Afterwards he wrote to his mother, "I could not think of it as you both disapprove, nor would I for a moment entertain the idea of marrying a girl without means to support her...but let me tell you this...however fickle you may think me, having once experienced what a woman's love is I can never forget it. I may never marry at all, but I'll never have anybody else, so bid goodbye to all your dreams of heiresses" (1844 November 26).
When the 46th embarked for Canada in 1845, David Fyffe was delayed by a court martial which required his testimony. To rejoin his regiment, he traveled on his own from the West Indies through New York to Nova Scotia, stopping along the way to see Niagara Falls. He was later transferred to the Depot in Ireland, where he finally had an opportunity to visit his family. In 1853, he was able to purchase a commission as major from a retiring officer. He died in 1858.