On September 30th, nearly thirty students from Boston International Newcomers Academy boarded World Ocean School’s schooner Roseway for an educational sailing program designed to expose underserved populations to tall ship sailing and colonial New England’s maritime history & heritage. Students participated in a sail where they engaged in seamanship activities and learned about Boston’s Revolutionary history, including the French Navy’s arrival to the colonies and the 1st Rhode Island Regiment, a military unit comprised in part of newly emancipated African Heritage and Indigenous men. This sail coincided with USS Constitution‘s turnaround cruise in Boston harbor, allowing for the extremely rare opportunity to learn about 18th- and 19th-century American history while sailing alongside the only 18th century American naval ship. Students also learned about the U.S. Navy’s Africa squadron, a fleet tasked with suppressing the Atlantic slave trade. Constitution served in this fleet, successfully capturing the slave ship H.N. Gambrill. The Revolutionary-era historical curriculum was compiled and delivered by Tall Ships America intern Brooke Grasberger, a PhD candidate at Brown University, while Tall Ships America program manager Nicolas Hardisty discussed the Africa Squadron and Constitution‘s exploits. Roseway‘s captain and crew enthusiastically taught students how to raise sails, handle lines, and shared their knowledge of maritime skills and safety. This partnership between Tall Ships America and World Ocean School was funded by a generous grant from the Washington-Rochambeau Revolutionary Route. Tall Ships America thanks Washington-Rochambeau Revolutionary Route Trail Administrator Johnny Carawan and World Ocean School Program Manager Tatiana Dalton for their work on this project.