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Canoe Racing on Maui: Sailing (and Paddling) into History

The author, ready to paddle off the coast of Maui.

By Tom Passavant

When I set off walking down Kaanapali beach around 3 p.m. on a recent Friday afternoon, my interest in Hawaiian sailing canoes was pretty much just intellectual. I had come to Maui to learn why a bunch of 45-foot long canoes, faithful reproductions of ancient Polynesian vessels, were so important to Hawaii’s culture and people today.  Ten of these canoes were taking part in an annual race across the entire Hawaiian island chain, and during their layover in Maui I hoped to get a chance to paddle one of the boats. Mostly, though, I’d “talk story” with the crews and learn about sailing traditions and the skills required to get from one island to another.

Twenty minutes later, I’d been recruited by skipper Matt Buckman to help sail his canoe, the La’amaomao, about a mile up the beach, where the next day the fleet would take part in Kaanapali Beach’s 8th annual sailing canoe festival, called Wa’a Kiakahi.  “We need some ballast,” Matt said, eyeing the whitecaps and the 20-knot winds. He forgot to mention that I’d also be the “sheeter”, the guy who holds the rope that controls the sail.

More than perhaps any other aspect of Hawaiian culture—including hula, surfing and the lyrical Hawaiian language—canoes are fundamental to who the Hawaiian people are and how they got to Hawaii in the first place. Tourists experience canoes via an outrigger ride at Waikiki beach, but locals paddle everything from sleek single seaters to four- and six-person racing canoes and even huge, double-hulled, twin-masted canoes capable of traversing thousands of miles of open ocean.

Ready to paddle.

“We realized there was no place on Maui for visitors to experience being on a canoe,” said Shelley Kekuna, executive director of the Kaanapali Beach Resort Association, which sponsors the three-day festival.  “This is an authentic Hawaiian experience that anyone can take part in.” Indeed, the mission of the Hawaiian Sailing Canoe Association [HSCA] is to “revive, educate and practice the ancient Hawaiian skills and values as they relate to the Hawaiian sailing canoe and its culture.”

At the moment, though, the educational experience I am most concerned about is keeping the La’amaomao from capsizing. As Matt struggles to steer with his big wooden paddle (the canoes lack both a keel and a rudder), I try to keep the sail under control. The strong offshore winds mean we’ll have to tack the canoe at some point, meaning I’ll have to jump from the trampoline-like net of the big ama across to the smaller “safety” outrigger on the other side of the hull. Eventually, soaking wet, I sort of get the hang of it and we sail far past our target before coming about and hurtling onto the beach.

When Captain James Cook arrived in Hawaii in 1778, he wrote of being greeted by a fleet of 3,000 canoes. “Canoes were used for inshore fishing, offshore fishing, travel along shorelines and between islands, and open ocean voyaging,” explained one of the Wa’a Kekahi crew members, Lemomi Kekian. When she’s not paddling, Lemomi teaches about voyaging canoes at a local community college. She also has the distinction of having crewed aboard Hokule’a, the most famous vessel in modern Hawaiian history. This 62-foot long, double-hulled canoe with twin sails, based on designs in ancient carvings, sailed to Tahiti and back in the mid-1970s, proving that ancient Polynesians had colonized the vast Pacific, including the Hawaiian islands.


Paddler Jane McKee.

Hokule’a, which has since completed dozens of voyages all over the Pacific, sails without any modern instruments at all, guided only by a navigator, or “wayfinder” whose skills are based on centuries of experience with the winds, waves, stars, and deep ocean currents. Hokule’a rewrote several centuries of misguided theory, showing that the Pacific islands were not colonized by aimless drifters on Kon Tiki-like balsa rafts launched from South America.  “That’s why we sail,” said Hokule’a’s first Hawaiian navigator, Nainoa Thompson. “So our children can grow up and be proud of who they are.  We are healing our souls by reconnecting with our ancestors.”

The day after my “holy sheet” shakedown cruise, I joined the Wa’a Kiakahi festivities and signed up for a short stint as a paddler on the Maui Jim boat. The crew members, both men and women, all look like they’ve just come back from a  “Pecs of the Pacific” photo shoot, and no wonder: paddling is a monster upper body workout. The race segments range from 30 to over 90 miles, across notoriously rough channels between the islands. No breaks for mai tais and pupus, either.

On Sunday morning, dozens of visitors and locals gather on the beach to watch the crews prepare to race to Molokai. The winds are still howling, and you can feel the tension as they eye the whitecaps just offshore. “This is not a young person’s sport,” notes Terri Galpin, HSCA president and captain of the all-woman boat Moa E Ku, which, appropriately, means “strong trade wind.” “To survive, you need to learn to leave all your mental baggage on the shore.” She ought to know: she and her crew once capsized off Oahu in fog and had to be rescued by the Coast Guard.

Finally, the sails are hoisted and the canoes pushed to the shoreline. Everyone, crewmembers and tourists alike, forms a circle and joins hands. Makalapua Kanula, cultural advisor for the Westin Ka’anapali Ocean Resort, offers blessings in Hawaiian and English. “You sail in the footsteps of our kapuna [elders],” she says. “May the winds be at your backs.” Then a whistle blows, and the boats, their sails snapping, crews paddling furiously, surge into the sea.

If You Go:

The Kaanapali Beach Resort area abounds with opportunities to connect with Hawaiian culture. Special programs highlighting dance, songs, star gazing, and historical walking tours abound. For more information about the resort and the Wa’a Kihaki festival, go to kaanapaliresort.com.

There are several hotels and condominium properties lined up along Kaanapali’s three miles of golden beach. I stayed at the Sheraton Maui Resort and Spa, set on 23 acres (!) of prime beachfront. The hotel, celebrating its 50th anniversary next year, is in tip-top shape. Don’t miss the sunset cliff dive from the 30-foot high Black Rock, a leap whose ideal accompaniment is a Cliff Dive Bar mai tai. Information: sheraton-maui.com.


Tom Passavant is a former editor-in-chief of Diversion magazine. Now a freelance travel and food writer based in Colorado and Hawaii, his work has appeared in Aspen Magazine, Gourmet, Four Seasons Magazine, Town & Country Travel, ForbesTraveler.com, Ski, Powder, Luxury Living, and many other places. He is the co-author of “Playboy’s Guide to Ultimate Skiing.” A former president of the New York Travel Writers Association, Passavant has won a Lowell Thomas Award for his travel writing and has served as judge for the James Beard Journalism Awards. See more of Tom’s work at TomPassavant.com.


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