The press frequently reported on his presence at Kennedy family events, such as the arrival of the Kennedy children in Washington in February 1961. He accompanied the President to church, launched a kite for the President's daughter Caroline, and delivered pet hamsters to the Kennedy children. He joined the President's entourage for his tours of Europe in both 1961 and 1963. In 1962 he escorted two of the President's sisters, Eunice Shriver and Jean Kennedy Smith, around Europe for more than two weeks. When the Kennedys spent the weekend at Glen Ora, their Virginia estate, Jacqueline Kennedy invited Billings to join them more often than the President did. She needed Billings to keep the President company while she went horseback riding.