He tried out for the football, golf, and swimming teams and earned a spot on the varsity swimming team. Kennedy also sailed in the Star class and won the 1936 Nantucket Sound Star Championship. In July 1937, Kennedy sailed to France—taking his convertible—and spent ten weeks driving through Europe with Billings. In June 1938, Kennedy sailed overseas with his father and older brother to work at the American embassy in London, where his father was President Franklin D. Roosevelt's U.S. Ambassador to the Court of St. James's.