Jessica Ferris can trace her interest in sailing back to her childhood in Chicago and northern Michigan, where she plied Lake Michigan's waters with her family. As she grew up, she expanded her boating territory to the Gulf of Mexico, the Caribbean, and the Atlantic and Pacific Oceans. As an adult, she brought her talents home to Chicago as an ASA-certified keelboat captain and the founder of Skyline Sailing School. Here, she passes on her seafaring knowledge in classroom courses that teach sailing principles such as basic terminology, rules of open-water travel, points of sail, knot tying, and choosing the right shoulder parrot. She also engages students with hands-on open-water classes aboard 26-foot keelboats, which begin with an exploration of basic sailing skills and progress to lessons in more advanced maneuvers.