Overview The Kanaka Ikaika Racing Association runs open-ocean paddling races out of Kailua, and its season builds to the Molokai Challenge, a 32-mile crossing of the Ka'iwi Channel from the west end of Molokai to Maunalua Bay on O'ahu, which KIRA bills as the world championship of open-ocean surfski and solo canoe racing. Around it sit about a dozen O'ahu races a year for outrigger canoes, surfskis, stand-up and prone paddleboards, among them a women's race, Na Wahine Ikaika, and the Lanikai Cold Pack Classic in December. KIRA is a volunteer-run nonprofit whose motto is 'By Paddlers For Paddlers.' On site The Molokai Challenge starts at 10:30 in the morning on Kaluakoi Beach at the west end of Molokai, after a pule at 9:30, and paddlers have to reach Portlock Point by 4:30 in the afternoon. It is raced solo in one- and two-person surfskis and outrigger canoes, or in relay teams of two to four, with an escort boat alongside: at least 17 feet, a captain and a spotter, checked in on VHF channel 72 before the start. Packet pickup runs at Hawaiian Island Creations in Ala Moana Center. The shorter races work O'ahu's coast: the Manu o ke Kai race runs 8 miles from Sunset to Haleiwa on the North Shore for everything from six-person canoes to single surfskis, and Na Wahine Ikaika runs from Hawaii Kai to Kaimana Beach. Audience The field is paddlers rather than spectators. The Poai Puni series counts each racer's best four finishes in OC-1, V-1, surfski, SUP or prone, so the same people come back race after race, and the top three men and women in each long-course discipline earn free entry to the Molokai crossing. Na Wahine Ikaika runs age groups from juniors of 16 to women over 30. Talent and Influencers The crossing draws the sport's best-known names. Oscar Chalupsky won it seven times between 1981 and 1989, Dean Gardiner four times in five years, Hank McGregor five times and Cory Hill four. McGregor set the men's record of 3:11:17 in 2019, the same year Jordan Mercer set the women's, 3:47:22. Track record The first crossing was Dale Adams paddling a kayak alone from Molokai in 1976, in seven and a half hours; KIRA formed around him and ran the first official race in 1977. The crossing ran for the 49th time in 2026. It began as a surfski race and added outrigger canoes, prone and stand-up boards, and relay divisions from 2015. Poai Puni points standings are archived back to 2014. Brand presence Sponsors ride in the race names: in 2026 the calendar carried Nico's, Kialoa, HIC, Puakea, Kai Wa'a, Outrigger Zone and Haleiwa Joe's in race titles, and the crossing ran as the Maui Jim Molokai Challenge. KIRA pays for the season from paddler fees, sponsorships, donations and grants.