Kaʻimiloa shared with and learned from various cultural practitioners such as Emil Wolfgramm, Royal Protocol Consultant representing the South Pacific Islands, Educator, and Professional Storyteller. She also mentored under the late ʻŌlohe Stephen Hauʻoli Kupihea, Master in the Hawaiian and Polynesian art of ancient hand-to-hand combat, warfare, and spirituality; Kumu Hula John Kaʻimikaua, Master of ancient Molokaʻi hula, Chanter/Historian; and Elia Kawika Kapahulehua, Master Seaman and First Captain of the Hōkūleʻa and Instructor of ʻŌrero Matuahine, the old Hawaiian language or our mother tongue. Kaʻimiloa has sat with Indian Elders of the Hualapai Nation, Arizona and Three Pius Sun, Medicine Man of the Stoney Nation (Alberta, Canada), and Tribal Spiritual Leaders and Artists of the Talaandig Village (Mindanao, Philippines).