In 1967, Charlie went sailing with his boss and became enamored with the sport. He purchased a 19-foot sailboat shortly thereafter and sailed and vacationed on it with his family of six for several years. He could not sit up straight in the cabin, so eventually he bought a 29-foot Bristol. Ultimately he worked his way up to his dream boat, a 35.5-foot Bristol and finally had headroom for his six-foot two-inch frame. Charlie sailed with his family to places like Nantucket, Cuttyhunk, Block Island, and Booth Bay Harbor, Maine.