At the 49th Grammy Awards in Los Angeles, California, on February 11, 2007, Kamakahi received his first Grammy Award for Best Hawaiian Album for the slack key guitar compilation CD Legends of Hawaiian Slack Key Guitar, part of the recorded live concerts at Kapalua, Maui, at the Ritz Carlton Hotel.
On February 11, 2007, during the 49th Grammy Awards in Los Angeles, California, Kamakahi won his first Grammy Award for Best Hawaiian Album for the slack key guitar compilation CD Legends of Hawaiian Slack Key Guitar, featuring live performances at Kapalua, Maui, at the Ritz Carlton Hotel.