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Hawaiian Sailing Canoe Racing

a boat on a body of water

a small boat in a body of water with a mountain in the background

a boat sitting on top of a beachOn our tours I often talk about how I got into Hawaiian canoe sailing in the first place, which led to our awesome tour here at Maui Sailing Canoe. I grew up racing outriggers on Oahu, paddling mostly for the Outrigger Canoe Club and Punahou School (it is an interscholastic sport here in Hawaii).


One summer I had a coach, Matt Buckman, for our U14 regatta season crew. During the summer he made a crew of a select few of us 13, 14, and 15 year olds, and with him steering we did the 100 mile Oahu to Kauai Na Holo Kai Hawaiian sailing canoe race. See, Matt was one of the original guys who started taking modern Hawaiian fiberglass canoes and rigging them up to sail inter island.


By the time I got involved, the Hawaiian Sailing Canoe Association had a season starting on the Big Island in May, and racing island to island all the way down the Hawaiian chain, finishing up on Kauai. This is an incredibly fun, exciting, and challenging endeavor to be involved in. My favorite race was alway the first race, Keokea, Big Island to Hana Maui – camp overnight in Hana – then on to Kahului Harbor the next day. The notorious Alenuihaha Channel is the deepest and roughest in all of the Hawaiian Islands, and sailing across it is a huge challenge.


During these races we would alway overload the safety equipment including EPIRB, VHF Radios, lifejackets, cell phones, plenty of water (and beer), and food. Escort boats would typically follow the racers across the channel just in case. I have been personally towed by one several times throughout my Hawaiian sailing canoe career.


There was alway a strong sense of community with the racing season. Everyone involved knew the risks, and everyone had each others’ back. It was a very tight knit group of people. Some of the greatest times of my life were flying across the channel in a Hawaiian sailing canoe going 20 miles an hour, soaking wet, overtaking swells…amazing.