Churchill took a three-month vacation to North America in the summer and fall of 1929, a little known event in his long career. In the company of his son Randolph, his brother Jack and his nephew Johnny, the Churchills toured Canada and the U.S. Notable events include Churchill's meeting with important figures in politics, business, newspapers and entertainment (President Hoover, Prime Minister Mackenzie King, Bernard Baruch, William Randolph Hearst and Charlie Chaplin) as well as his visits to such natural landmarks as the Grand Canyon, Lake Louise, Niagara Falls and Yosemite.

The Churchills also visited a lumber camp, slaughterhouse and steel factory, went fishing on the Pacific Ocean and inspected the battlefields at Quebec and Virginia. On the visit Churchill endured prohibition in America and gambled on the stock market. It was on this trip of course that Churchill gained an understanding of the two countries firsthand and formed his opinions of Canada and the United States.