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Sport: Seasoned Pros

Shawna Cropas, a fashion model turned triple-crown windsurfing champion, peers nervously across Maui’s southwestern shore. “See the clouds over the mountain?” she says, gesturing to an ominous bank looming in the early morning sky. “It means it’s already windy on the North Shore. We should leave earlier!”

Maui, especially the windward side of Haleakala Crater, is perpetually blustery because of northeasterly trade winds. The conditions help make Hawaii’s second-largest island one of the world’s premier destinations for windsurfing, but today’s gusts are different. The wind is onshore—and uncharacteristically strong. “This is storm weather,” Cropas says with a trace of concern, knowing this is my first windsurfing lesson. “But this is part of windsurfing. You have to deal, but you are safe.” 

Cropas, a Vancouver native, along with her close friend and business partner, Matt Pritchard—a world windsurfing champion who has won titles in both the Super X and freestyle divisions—have offered multiday lessons for the last three years through their Maui-based company, Aloha Windsurfing Clinics. This fall, the pair, who have more than 44 years of combined experience, are partnering with the Four Seasons Resort Maui at Wailea to host the ultimate crash course in the sport. From November 10 through 15, eight guests of the oceanfront property will learn firsthand from the pros during a windsurfing clinic that is part of the resort’s Unforgettable Events series, which strives to deliver authentic and uniquely Hawaiian experiences. “Maui is windsurfing, but this is not your typical one-hour lesson,” Cropas says. “No one else is doing this.” 

The Four Seasons’ $5,950-per-person program includes accommodations at the 380-room resort as well as meals and gear rentals. Daily instruction both on land and in the water will be followed by video and still-image analyses.Participants can also develop core muscles and balance through optional stand-up paddleboarding sessions, and can take an afternoon excursion to Ho’okipa—the top windsurfing beach in the world—to witness the pros in action on waves that average from 15 to 20 feet.

Considering the advanced conditions on my first morning, Cropas and Pritchard select a slightly protected cove on the eastern end of Kanaha Beach for my lesson. Following a series of practice drills on the sand, I put my new skills to the test in waist-deep water. Once on the board, I frantically try to control the sail, but I repeatedly lose the game of tug-of-war with the wind. The more I fight, the quicker I splash back into the water, frustrated and struggling to reposition the sail to the leeward side of the board.

Cropas and Pritchard coach me through the process, nurturing but determined to help me master the dance between wind and sail. “Be Zen,” Pritchard says. “Blow like a tree in the wind, or snap your branches. And don’t forget to breathe.”

By the second day of instruction, I am more comfortable easing onto the board and slowly grabbing hold of the boom. I begin moving in unison with the sail through the choppy waters, falling into a rhythm and feeling sure-footed and safe, if not quite like a pro.

Four Seasons Resort Maui at Wailea, 808.874.8000, www.fourseasons.com

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