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It’s funny how a good day of wind, or in Greg Mebel’s case, a deep day of powder, can profoundly alter but not finalize the natural trajectory of one’s life. Having grown up in Boston, Greg spent his college years at Northwestern University on the shores of Lake Michigan. Working at the college’s sailing center, he quickly learned the lifestyle benefits of windsurfing instruction; you can’t teach on the windiest days, effectively clearing your schedule for the best sessions. Intending to follow his passion for windsurfing, he applied for an instructor job at a Caribbean resort, and while the New York office was processing his job application, he took a side trip to visit a friend in Aspen. As fate would have it, the Caribbean called shortly after his first powder day, but at 8000 feet, Greg was already sold on mountain life with nine months of winter sports ahead of him.

As the ski town years unfolded, Greg worked his way up into a role as the publisher of the town’s daily newspaper. With its upscale clientele, Aspen is an expensive place to live, yet journalism put Greg at the center of every issue and provided access to a lot of resources, making ski-town life an addictive blast. On his transition from windsurfing to kiteboarding, Greg recalls three years doing the ‘go on a windsurfing trip and take some kite lessons’ routine. On one vacation to Puerto Rico, he remembers his girlfriend, now wife, chasing him through the backstreets of San Juan, trying to track his errant downwinder. It wasn’t until another trip that Greg, determined to leave Baja as a competent kiter, camped on the beach in La Ventana for six weeks without any windsurfing gear and finally crossed the kiteboarding threshold.

It has been said that Greg Mebel chose his college based on the quality of its windsurfing facilities. From a small mountain town to Maui’s North shore, Greg has spent his entire life faithfully following the wind. // Photo Nate Volk

In 2007, after 10 years at the Aspen Daily News, Greg followed his wind-born impulse to pursue a three-month pilgrimage to the windsports mecca of Maui. Having stayed long enough to score some good waves at the end of the summer season, he and his wife hit pause for 13 more months and then spent the next four years splitting their time between Aspen and Maui. When they finally committed to Maui full time, the couple landed a gig managing the Nalu Kai Lodge in the heart of Paia, a ritual waypoint for many kiters and windsurfers exploring the island. Returning to their scrappy days as ski/surf bums, Greg started writing for some local newspapers and got a part-time job guiding ‘fresh off the boat’ tourists down Haleakala on bicycles. Having researched the stories that other guides were telling, Greg realized, “there was absolutely no correlation between truth and tips; it only mattered how fun the tour was and the quality of the jokes.” Removing his journalism hat, Greg transitioned his shtick away from interpretive history and focused on producing an entertaining show. Looking back at the good times, he reminisces, “I loved getting up on the volcano every day; it was the best of both worlds.”

Greg and his wife reflect on their time at the Nalu Kai Lodge with fondness; it was a clearinghouse for kiters and windsurfers coming to Maui from all over the world. Living at the lodge and managing reservations, Greg eventually found himself in the vacation rental business. His version of the trade often involved showing people around, sharing intel on local kite spots and making sure they received the proper instruction to stay safe and have a good time. When the island’s laws regarding vacation rentals shifted, Greg followed the path of least resistance towards his realtor’s license. With no lack of irony, Greg points out the contrast between his background in small ski town journalism and his current line of work in tourism-related real estate. Having presided over the divide between objective news reporting and commercial advertiser interests, he’s keenly aware of the paradox of his path.

Nowadays, he helps newcomers settle into their own version of island life and points to the excitement in his clients’ voices when they experience a long downwinder or score their first session in Hawaiian waves. Greg admits, “The best part of the job is sharing the stoke of kiteboarding and hooking clients up with the right setup and connections.” While introducing people to Maui’s world-class windsports and handing over the keys to island life, Greg prides himself on building community within Maui’s kiteboarding tribe and keeping his options open for the windiest days and the best waves.

If you need Greg’s help getting set up on Maui, you can find him at: www.gm-re.com

This article was featured in our fall 2021 issue, Vol. 18, No. 3. To read more, click here.