I have always wanted to go there, as I have felt that it is not just another college, but is a university with something definite to offer. Then too, I would like to go to the same college as my father. To be a 'Harvard man' is an enviable distinction, and one that I sincerely hope I shall attain."[24] He produced that year's annual "Freshman Smoker", called by a reviewer "an elaborate entertainment, which included in its cast outstanding personalities of the radio, screen and sports world".[25]
He tried out for the football, golf, and swimming teams and earned a spot on the varsity swimming team.[26] Kennedy also sailed in the Star class and won the 1936 Nantucket Sound Star Championship.[27] In July 1937, Kennedy sailed to France—taking his convertible—and spent ten weeks driving through Europe with Billings.[28] 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.