The Sailing Diary contains accounts of two voyages made by an unidentified man in the nineteenth century. The description of the first trip begins with the writer's arrival in New York on July 15 [1857]. The writer departs New York on July 21, aboard the steamship Webster, bound for Liverpool via Newfoundland. He describes daily life aboard the ship, including shipboard operations, provides weather conditions and mentions any noteworthy events, especially encounters with sea life (porpoises, whales, and birds) and other ships. He often mentions his family at home and the tedium of being shipboard for an extended time, likening it to a prison, and often plays euchre with other passengers and the captain. The diary continues through the ship's landing at Liverpool on August 17, with the writer describing the city before departing for London shortly thereafter. The account ends with the writer anticipating his upcoming trip to Rotterdam.

The second account commences on February 10, 1872, with the writer aboard the steamship "Yasoo" (almost certainly the Yazoo), being assisted out of an unidentified port (possibly Philadelphia) by an iceboat and tugs. Through the course of the voyage, he recounts weather conditions, his seasickness, onboard accidents, and encounters with other vessels, as the ship continues down the east coast. The writer is given permission to go ashore in an unidentified city (possibly Havana, Cuba), which he describes. The account ends abruptly on February 19, with the writer anticipating his arrival in New Orleans.