Initially interested in architecture, he attended Principia College in Elsah, Illinois where he ultimately studied fine arts and character education, graduating with highest honours.
Nicknamed "Gershwin" in college, he studied piano for ten years with Delaine Counseller in Lansing, Michigan, pipe organ for four years with Dr. John Near at Principia College, and carillon with Belgian carillonneur Carlo Van Ulft of Centralia, Illinois. Both of Gershwin's parents are British traditional folk-singers, and he shows a love for that style of music as well, playing guitar and belting out sea chanteys.
Gershwin grew up sailing his family's 19' Flying Scot, Skye, on a small inland lake in Michigan. He began his professional sailing career in 2000 aboard the wooden schooners Grace Bailey and Mercantile, built in 1882 and 1916 respectively, sailing multi-day windjammer trips with tourists along the coast of Maine.
He has also worked as a deckhand aboard the M.V. Illusions and S.V. Sea Shell in the Seychelles, Indian Ocean; as first mate and captain on the schooner Manitou in Grand Traverse Bay and Northern Lake Michigan; and most recently as captain of the Friends Good Will, a replica of an 1810 square-tops'l sloop built for the Michigan Maritime Museum in South Haven, Michigan.
Gershwin enjoys many other hobbies; some of which include knitting, sewing, cooking, reading, writing, and dabbling with foreign languages.