At Annapolis, Shepard enjoyed aquatic sports. He was a keen and competitive sailor, winning several races, including a regatta held by the Annapolis Yacht Club. He learned to sail all the types of boats the academy owned, up to and including , a schooner. He also participated in swimming, and rowed with the eight. During his Christmas break in 1942, he went to Principia College to be with his sister, who was unable to go home owing to wartime travel restrictions. There he met Louise Brewer, whose parents were pensioners on the du Pont family estate, and, like Renza Shepard, were devout Christian Scientists. Owing to the war, the usual four-year course at Annapolis was cut short by a year. He graduated with the class of 1945 on June 6, 1944, ranked 463rd out of 915, and was commissioned as an ensign and awarded a Bachelor of Science degree. The following month he became secretly engaged to Louise.