As a successful businessman, Simeon sent his children to private schools. At age seven, John attended Elizabeth and Alexis Ferms' "Children's Playhouse" school, an experimental school for children. Later he and his siblings went to Halstead School in Yonkers, New York and then to Cutler School in New Rochelle, New York. In 1906, Simeon sent the three children on a tour of Europe, and seeing theatre was on the list of activities. John Howard took notes on the set designs, actors, and plays. In 1909, they were sent on a tour of the United States and Canada.