Hellbent for Hawaii

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.