The first modern-day Hawaiian sailing canoe race took place in 1987: Na Holo Kai, a heady, ninety-mile channel crossing from O‘ahu to Kaua‘i made by nine canoes. Carlos Andrade was one of the organizers, inspired by the fact that 1987 was the “Year of the Hawaiian.” The slack key virtuoso had just served as a crew member aboard the voyaging canoe Hokule‘a on its 1986 journey from New Zealand to Tonga and Samoa.
The sailing canoe is one of the Pacific’s great engineering feats and cultural archetypes. Sailing canoes have multiple designs, each adapted for its particular function: There are the large canoes like Hokule‘a, which made the watershed 2,500-mile voyage from Hawai‘i to Tahiti in 1976, navigating entirely by Polynesian wayfinding. Voyaging and war canoes exceeded lengths of eighty feet to carry passengers and provisions, warriors and weapons. Then there are smaller canoes, which in olden days were used for fishing and transporting supplies and people around and between the Islands. For everyday life, even more compact designs—like the twenty- to thirty-foot single-hull sailing canoes used to catch ‘opelu—sufficed.
The racing canoes used today, though built from modern materials, were inspired by those smaller traditional canoes. In essence today’s racing canoes are modified six-person outriggers, with a hull typically forty to forty-five feet long, a mast between the first and second seats, and a second, smaller ama (outrigger float) added to provide greater stability. A trampoline that stretches from the main ama to the canoe becomes the platform from which the sheet man trims the sail.
In those early years of modern canoe sailing, the races had a freewheeling, sail-by-the-seat-of-your-board-shorts quality. In 1988, the second year of Na Holo Kai, Cappy Sheeley was living on Maui when he got a phone call from Mike Spalding suggesting they compete. Never mind that they didn’t have a sailing canoe. There were only a handful of canoe sailors around the Islands, most of them resourceful paddlers who’d simply raised a mast and thrown up a sail. If they could do it, Spalding insisted, there was no reason he and Sheeley couldn’t—and with the prospects of a $10,000 first prize, they couldn’t resist trying.
Though the two had met only briefly, Spalding was confident that together they could assemble a winning vessel and crew. Sheeley was an exceptional waterman who’d competed in two Olympic trials: swimming in 1964 and sailing in 1976. He’d learned to race catamarans with Duke Kahanamoku and Woody Brown in the 1950s. (Brown, inspired by double-hulled Polynesian canoes, built the first modern ocean catamaran in 1947, a design that predated the Hobie Cat and outraced the fastest single-hulled yachts in the Transpac regatta.) What’s more, he was an accomplished paddler and part of the winning crew in the 1970 Moloka‘i Ho‘e.
“Let’s go for it. Let’s see what we can do,” Spalding convinced Sheeley. They borrowed $5,000 from the bank to buy the hull and constructed the rest themselves. The canoe was finished a week before the race, leaving little time to figure out how to actually sail it. The dress rehearsal took place when they crossed the channels from Maui to Moloka‘i to O‘ahu, all to get to the starting line at Wai‘anae’s Poka‘i Bay.
The race to Kaua‘i was grueling. The name Na Holo Kai suggests a swift run across the sea, but the 1988 run was any-thing but—the winds were extremely light, and the contest became a paddle battle. “We were lucky to get into a squall, and we stayed in it as long as we could,” Sheeley recalls. “It turned into an endurance contest. I think we won because we had more [drinking] water in the boat.” They arrived at N awiliwili Harbor after ten and a half hours, just as the sun was setting.
On a good day it’s very different. “Canoe sailing reminded me of cat sailing. You’re low to the water,” Sheeley says. He describes what it’s like when there’s some swell and the wind is clocking twenty-five knots: “The spray’s coming up on both sides, and the canoe is on its feet. The water’s moving so fast, and you hear it tapping—shhks, shhks, shhks—against the canoe.”
He compares the channel crossing races to endurance events like the Ironman. “But obviously,” he laughs, “I think it’s better because you’re getting wet. And then there’s the survival aspect. You’re in between islands. You can’t stop. You have to get to the end. People who are successful at this sport are the ones who can do things for hours at a time.”
A sailing canoe crew of six must have an experienced sailor to control the sheet and a keen steersman who can negotiate rough water, read the swells and pick a favorable course. “The steersman and the sheet man have to work in unison,” Sheeley says. “And all six people have to work together to make the canoe go fast.”
The Na Holo Kai is a tough race. But for extreme athletes like Sheeley and Spalding—who has swum across seven of Hawai‘i’s nine channels—it’s fun.
“Isn’t that what makes something exciting, the fear that you might fail?” Sheeley muses. Canoe sailors possess a sense of humor, a staunch will and nerves of steel. These are guys like Ronnie Kang, who fashioned his own paddle from plywood and resin and stroked it more than 4,000 nautical miles before it snapped. Guys like Kendall Struxness, who steered the outrigger sailing crew that collectively paddled 461 miles through the Northwest Hawaiian Islands for eighty-three hours straight from Mokumanamana to Laysan Island. Guys like Gaylord Wilcox, who, after being bucked off a canoe, spent the night floating two miles off Moloka‘i before a sailboat rescued him the next morning (“I think after that everyone started carrying lights,” Sheeley chuckles). Guys like Matt Buckman, who boarded a plane wearing duck fins when the airline demanded he don footwear.
“Canoe sailing is the most fun you can have in the water in downwind conditions. It’s amazing to go that fast, surfing big, open-ocean swells, having waves crashing over you and trying to avoid getting slammed,” Spalding enthuses, explaining why in 1989 their crew signed up to race Na Holo Kai again. For five consecutive years they dominated the event, reaping the acclaim of being the fastest canoe on the ocean.