The Apprentice Boy was built at Milwaukee by J. Bamler (listed in some places as Barber) and enrolled there in 1867 with its homeport listed as Grand Haven, Michigan. Upon enrollment, it had a gross tonnage of 208 tons and was owned by Kirby, Furlong & Co. It underwent significant repairs in 1871. The ship was sold in 1884 for $3,500, by then-owner Senator T.W. Ferry and the Michigan Barge Company, to brothers Henry and Daniel O'Brien. The O'Brien brothers kept the line in Grand Haven and Chicago. The bottom was recalked in 1887.

The Apprentice Boy was involved in a serious collision in November of 1891. While making harbor at Manitowoc, it collided with the Windsor. The Apprentice Boy only suffered slight damage to the bow, but the Windsor was damaged so severely that it sank shortly afterward. The bottom was recalked again in 1895 at Chicago. It was involved in another collision on August 8, 1896, with the schooner C.L. Wrenn, between Port Washington and Milwaukee. It was reported that, upon making port in Chicago, the Apprentice Boy was leaking badly. It apparently survived the collision, however, as it continues to appear in historical records following the event. In 1897, it received repairs and recalking in the Independent Tug Lines' floating dry dock. It reportedly wintered at Chicago in 1900, owned by John Peil. In 1906, ownership was transferred to Tebo Coal Company.
The Apprentice Boy was reported ashore or foundered in several different places. One of the earliest reports dates to 1869, and states the schooner went aground near Wolf River in Lake Michigan, while carrying a cargo of lumber. It was described as a total loss. During a storm in 1873, the Apprentice Boy reportedly went ashore near Grand Haven, alongside other vessels Magnolia and C.C. Butts. Another source found the Apprentice Boy ashore near Portage, Wisconsin, where the Sturgeon Bay ship canal was to be built. In 1910, however, the Door County Advocate reported that the vessel was used to fill in the old Wabash slip in Chicago.
The current location and condition of the Apprentice Boy wreck has yet to be determined by archaeological investigation.