Tabor aims to have every one of its students participate in an experience aboard the SSV Tabor Boy at some point during his or her school career. Some students will do so by signing on as part of the schooner's crew and will elect Tabor Boy as their fall and spring co-curricular activity each year. Others will experience two weeks aboard ship by participating in the Caribbean Studies Program that is offered every third year. Most students, however, will find their way aboard the Tabor Boy as one of the very first things they do after deciding to enroll at the school.

Each summer Tabor offers all incoming students a one-week sailing adventure aboard the schooner. Each week of this "Orientation at Sea" program brings together twelve to fourteen students, Tabor faculty members, and student crew members for six days of sailing, exploring, and learning along the coast of Maine. For new students the cruise is a great introduction to Tabor. They have the opportunity to make friends with classmates, teachers and returning students before starting school in the fall, and to gain a general introduction to oceanology, marine biology and environmental studies. As part of the vessel’s crew, students learn to handle sail, stand watch, steer a course, and take part in various other duties of manning a large sailing vessel.