In March 1922, during his junior year at IU, Pyle and three of his fraternity brothers dropped out of school for a semester to follow the IU baseball team on a trip to Japan. Pyle and his fraternity brothers found work aboard the S.S. "Keystone State". During its voyage across the Pacific Ocean, the ship docked at ports such as Shanghai, Hong Kong, and Manila, as well as in Japan before returning trip to the United States. Pyle's interest in traveling and exploring the world would continue in his later years as a reporter.