The owner of the business, Wendy Costa, holds a U.S. Coast Guard Master's license for a 50-ton inspected vessel and American Sailing Association certifications 101 and 103 (Basic Keelboat Sailing and Intermediate Keelboat Sailing). She serves as a part-time captain / teacher on historic wooden workboats at Echo Hill Outdoor School, and she is also an occasional co-leader of kayak excursions at Chester River Kayak Adventures. She has 25 years of teaching experience, from 6th grade through college.

Wendy has spent part of every summer of her adult life boating on the Sassafras River and the Upper Chesapeake Bay. Wendy Costa built the Passagemaker dinghy (used by the business for sailing lessons) at Chesapeake Light Craft, and she was one of the first people in the area to own and sail a Hobie Mirage Adventure Island sailing kayak.

Wendy Costa holds a B.A. in American Studies from Vassar College, an M.A. in American History from Columbia University, and an Ed.D from The University of California at Davis.