Twenty-two and a World War II widow, Dorothy Estermann resolved to build a new life. It was 1944 and she was working as a secretary for the Commonwealth Edison Company. Joining a tour group that was traveling to Mexico seemed like a good start. It was Dorothy's first trip outside the U.S., and as it would turn out, the beginning of a lifetime of travel and adventure.

In the years that followed, Dorothy explored the western U.S., Canada, and the Caribbean. She traveled to New York and revisited Mexico. In 1948, she took the big step of leaving her hometown of Chicago and moving to Los...