[5] In 1849, he and schoolmate Charles Hastings Judd, as children of ministers of the cabinet of Kamehameha III, attended the Royal School.

[6] When he was 15 years old, his mother accompanied him to the mainland United States,[7] where he was enrolled in the university preparatory Phillips Academy at Andover, Massachusetts.

[8] A graduate of Yale University, he studied law under the tutelage of his uncle, Massachusetts Supreme Judicial Court Chief Justice Reuben Atwater Chapman.

[13] Shortly thereafter, he was invited to participate in Kalākaua's 1881 world tour, an endeavor to encourage plantation labor immigration to Hawaii.

[15] It was his responsibility to compile a feasibility study of each country they visited, reporting back on which nations were likely to provide "a desirable population" for the Hawaiian labor force.

Together with Chamberlain Colonel Charles Hastings Judd, and cook Robert von Oelhoffen, they circumnavigated the world from February 22 to October 29, visiting Asia, the Mideast and Europe.

At the end, they took a railroad train trip from the east coast of the United States to California, and sailed back to Hawaii.