Born into Hawaiian nobility, Kawānanakoa grew up the royal court of his uncle King Kalākaua and aunt Queen Kapiʻolani who adopted him and his brothers after the death of their parents.

On multiple occasions, he and his brothers were considered as candidates for the line of succession to the Hawaiian throne after their cousin Princess Kaʻiulani but were never constitutionally proclaimed.

Kawānanakoa was born February 19, 1868, at Kaʻalaʻa at the mouth of the Pauoa Valley, in Honolulu, on the old homestead of his aunt Queen Kapiʻolani.

The family split their times living with the king and queen on the premise of the old ʻIolani Palace or at Kapiʻolani's private residence Pualeilani in Waikīkī where the Hyatt Regency Waikiki now stands.

[14][15] On February 10, 1883, Kawānanakoa was granted by letters patent the title of Prince and style of His Royal Highness by King Kalākaua along with his mother, brothers and aunt.

The king also furthered outlined that he wished in the case that the throne passed to Kawānanakoa or his brother that they "assume the name and title of Kalakaua, and to be numbered in order from" him.

[21][22] On Article 22 of proposed 1893 Constitution of the Hawaiian Kingdom, Queen Liliʻuokalani outlined the succession to include Kaʻiulani followed by Kawānanakoa and Kūhiō and their legitimate heirs.

[29] In September 1890, Kawānanakoa and Kūhiō became the first surfers in the British Isles and taught their English tutor John Wrightson to surf on the beaches of Bridlington in northern England.

[30][31][32] On August 31, 1891, Queen Liliʻuokalani appointed Kawānanakoa as a member of her Privy Council of State, a constitutionally-created advisory body purposed to advise and consent to acts made by the monarch.

[3] Liliʻuokalani was overthrown on January 17, 1893, and the Provisional Government of Hawaii established under pro-annexation leader Sanford B. Dole was officially recognized.

[36] A pro-annexationist delegation headed by Lorrin A. Thurston was sent by the provisional government for Washington, D.C., on January 19, to lobby for immediate annexation by the United States.

Archibald Scott Cleghorn paid for the travel expenses of Edward C. Macfarlane, another of the queen's envoys, to protect the rights of his daughter Princess Kaʻiulani.

[41] While in New York, Kawānanakoa also visited his cousin Princess Kaʻiulani, who was in the United States to protest the proposed annexation of Hawaii, with her guardian Theophilus Harris Davies.

On January 6–9, 1895, supporters of the monarchy launched an unsuccessful counter-revolution led Robert William Wilcox to restore Liliʻuokalani to the throne.

Documents presented against the former queen at the subsequent trials included signed commissions for a restored monarchial government with Kawānanakoa and Kūhiō as governors of Maui and Kauai, respectively.

[50] His brother Kūhiō played a more active role in the rebellion and was found guilty by a military tribunal and sentenced to one year imprisonment.

President Dole handed over "the sovereignty and public property of the Hawaiian Islands" to United States minister Harold M. Sewall.

[59] In the subsequent election cycle, his younger brother Kūhiō (who was a former member of the Home Rule Party) joined the Republicans while the Democrats including Kawānanakoa allied with Wilcox.

According to the report, the betrothal was dependent upon the finalization of deeds to a sizeable real estate holding, transferred from Queen Kapiʻolani to both Kawānanakoa and Kalanianaʻole.

[67] On January 6, 1902, Kawānanakoa married Abigail Wahiʻikaʻahuʻula Campbell in a Roman Catholic ceremony officiated by Patrick William Riordan, Archbishop of San Francisco at the Occidental Hotel.