Join Our Team
The Apprenticeshop is a community that cultivates thinkers, makers, and doers through traditional boatbuilding and seamanship to navigate an ever-changing world. We believe that all people are capable of building and sailing boats, and that in the process, they develop resilience, self-confidence and resourcefulness. The educational experience at the Apprenticeshop is truly hands-on, with the majority of learning happening through direct experience rather than through traditional class-based teaching. We embrace the idea that there isn’t one right way to build or sail a boat. We teach by providing opportunity for discussion and group problem-solving, as well as room for innovation and creative thinking.
Open Positions
Adult Sailing Instructor
Our seasonal sailing instructors teach beginner through advanced sailing aboard our fleet of (mostly) traditional wooden boats. This is a flexible, hourly, seasonal position (June–September, starting at $22/hour) perfect for passionate sailors who love sharing their skills with individuals, families, and small groups. Instructors work closely with the Program Director and Community Waterfront Director to create engaging, hands-on experiences on Rockland Harbor’s waterfront. Ideal candidates have strong small-boat sailing and powerboat handling skills, teaching/coaching experience, and a USCG OUPV license or equivalent.
Read the full position description and application instructions here.