John D. Whidden served in various roles on ships since the age of twelve. Although he portrayed himself as a roguish boy, he quickly proved himself as a ship's gofer, and earned a mate's position by his early twenties. His travels saw him around the world, with stops at major ports such as Honolulu, Buenos Aires, Calcutta, and Liverpool. His life spans the changes in the shipping industry over the 19th and into the 20th century. During the Civil War, Whidden was heavily involved in profitable island trading in the Bahamas to elude Confederate sailors. However, shortly after the close of the war, in 1870, Whidden left sailing as he found it being overtaken by foreign interests. He wrote this work in 1908, partly as a memoir, but also to offer a snippet of the "old sailing ship days" before major changes occurred to its business environment, fundamentally changing its nature.