Hellbent for Hawaii
There’s more than one way to sneak in a round of golf. You could stretch a business trip by half a day. You could tee off at sunrise and still get to your desk by 9 a.m.

That’s standard stuff.

Or you can rent a small plane similar to a WWII Japanese Zero, which seats two—pilot and co-pilot—one behind the other so the co-pilot’s legs are wrapped around the pilot’s seat. The plane has no storage compartment, so the only way to cram two sets of clubs is to slide the individual sticks, one by one, between the seats and the fuselage, then somehow stuff bags in around them. Now fly this antique aircraft over hundreds of miles of open ocean, land at a leper colony and make your tee time.

That describes just one leg of a lunatic journey in the goal of Washington D.C.-based Jon Cummings’s goal of playing every course in Hawaii. He started his quest in the early ’90s, making return trips to keep up with new course opening.

The obsession began fairly innocently. Living on Oahu in 1990, Cummings set himself the goal of becoming one of the very first to play both of the two newly built standouts on Lanai—the Experience at Koele designed by Greg Norman and the Challenge at Manele crafted by Jack Nicklaus. He took a commercial flight to Lanai, but ran out of daylight before he could get down the mountain to play Manele. So he flew home to Oahu, then flew back to Lanai the next day. On his way home, grander plans began to form.

Overlooking the golf compulsion, Cummings seems basically sane. He is an accomplished amateur pilot, an engineer specialized in stealth propulsion systems for submarines and a talented bluegrass guitarist. He’s an ever-inspired golf partner and has managed to befriend members of the most prestigious clubs in America. That trait has been Cummings’ ticket to Cypress Point, Oakmont and Pine Valley.His recordkeeping is as extensive as his zeal. Cummings has saved the scorecard from every single round he’s played. Through last year, Cummings had played 707 different golf courses in the U.S. and the United Kingdom.

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“It helped to be an amateur pilot,” says Cummings. It also helped to have a Hawaii driver’s license, which earns discounts on green fees at off-peak times. And a flexible work schedule.

The most dramatic golf course in Hawaii, in Cummings’ opinion? The Prince course at Princeville Resort on Kauai, where rainbows appear over canyons between green and tee. The most difficult is Ko’olau on Oahu’s east side. “It was designed as a super-exclusive hideout,” he says, “but turned out so tough it didn’t attract many members at the $250,000 initiation fee.” It re-opened as a public facility with a Slope Rating of 162. Rule of thumb there, Cummings warns, is one lost ball for each stroke of your handicap.

Cummings bestows his best-views-in-the-Islands awards to Wailea and Makena on the southwest of Maui. Both overlook Molikini and Kahoolawe and offer up-close looks at breaching whales in the winter. His preferred golf day off the beaten path would be Waimea Country Club, also on the Big Island. “It’s an un-Hawaii-like golf experience—you’ll feel like you’re playing on a ranch in Montana,” he notes.

His Hawaii highlight reel flickers on.

“You can also play golf at its most basic at Kahuku Municipal Golf Course on Oahu where $4 to play on grazing land may seem a bit exorbitant. You can play an Arnold Palmer course, Hapuna, that’s shoehorned into a mere 42 acres, or you can crowd onto one of the most abused courses in the world, Ala Wai Golf Club, which handles a staggering 185,000 rounds a year.”

If you’re like Cummings, you can keep a meticulous diary of every shot you’ve played. You can pile up boxfuls of scorecards in your basement. You can jam yourself into a Japanese Zero with a buddy and put your life on the line for a golf game. You just won’t be the first guy to do it.

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