“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.