The Sigsbee is a traditional Chesapeake Bay skipjack, a sailing craft designed and built to dredge for oysters. Skipjacks typically have a flat or v-shaped bottom and a shallow draft. The one self-tending jib and large triangular mainsail make these vessels easy to sail with a small crew. Today, skipjacks represent the last remaining commercial sailing fleet in the nation.

Originally built in 1901, the Sigsbee served in the oystering fleet for 88 years. The vessel is notable for the fact that in the early 1980s, it became the first skipjack captained by a woman, Leigh Hunteman of St. Michaels. In 1990, the Sigsbee became disabled near the Key Bridge during the annual Chesapeake Appreciation Days skipjack race. The owner, Douglas Darby West, then sold the boat to the Living Classrooms Foundation.

Students and shipwrights in the Save Our Skipjacks program spent 10 months reconstructing the vessel. The only original parts of the boat remaining include the mast step, hardware, and sails. Today, Sigsbee sails as part of the Living Classrooms Foundation's educational fleet, serving thousands of students per year.