Maui Wowi: the Island of Lanai is the Hawaii of Your Dreams

We were slinking up a series of narrow switchbacks, rising along red-clay cliffs from Shipwreck Beach on the way to Lanai’s only town. The sun high and bright, we dropped the convertible top of our rented Jeep and barreled south along a narrow path that traced the spine of Maunalei Gulch. Negotiating a dozen hairpin turns, hands 10 and 2, we didn’t notice that dark grey clouds were busy crowding out miles of blue sky. Moments later, the temperature plummeted a dozen degrees, the clouds unloaded their ballast, and we were drenched, still puttering along rutted dirt road, top down, in the thick of an unexpected downpour.

We took refuge under a tall Cook pine and a clump of highland spruces, then struggled unsuccessfully with the ragtop’s rusty zipper. Passengers of the only two cars that passed us stopped to offer help, which my male chromosomes instinctively refused. Instead, we waited sheepishly for the rain to pass then drove our muddy Jeep back to the sole rental car agency on the island.

“This happens all the time,” the agent told us, retrieving a special church key he used to pry the rusty ragtop zipper back along its track. “You’ve got to have one of these.”

Here’s another key you’ll need during your time on Lanai: a different mindset than on the rest of Hawaii.

Though you can make out the edges of Maui in the near distance, Lanai is no mini-Maui. Lanai has one tiny town, two paved roads and just 3,000 people, most of whom, you’ll quickly discover, know each other. Residents are quick with a handshake, a friendly wave as you pass on the road, and genuinely seem to welcome you with Aloha spirit. On Lanai, you’re only a stranger for a few minutes after you arrive. Hard to believe for an island that didn’t see tourists until 15 years ago.

Until 1992, nearly all of Lanai’s 140 square miles were operated as a Dole pineapple plantation. According to Kepa Maly, the executive director of the Lanai Cultural Center, the Castle and Cooke Company, one of the largest landowners in Hawaii, still owns 98 percent of the island. Castle and Cooke transitioned Lanai from pineapples to tourism and real estate in the early 1990s, retraining the locals to work in the hotels instead of the fields. In 1991 and 1992, the company opened Lanai’s two resort hotels, the Lodge at Koele, a 102-room, inland, hilltop hotel a mile from the ocean, and the 236-room, beachside Manele Bay Hotel; both were reflagged as Four Seasons resorts in 2005.

Dole harvested its last crop of Lanai pineapples in 1993. “Now, you won’t find a single pineapple growing on any of the 18,000 acres that used to be crop land,” Maly said.

It may be impossible to find a pineapple growing wild on Lanai, but it’s easy to find outstanding golf. Just head to one of the Four Seasons, the only two hotels on the island with more than a handful of rooms.

The Four Seasons hotels anchor Lanai’s two golf courses. Both are stunners, easily among the best in all of Hawaii. Both couldn’t be more different.

Jack Nicklaus laid out his cliffside Challenge at Manele on the edge of the Pacific, adjacent to the sprawling, beachside Four Seasons Manele Bay. The manicured landscape seems perfectly married to the land, coasting along the top of the old lava flow – that is, until you round a bend at No. 14, where you cross a daunting desert chasm so parched and rocky that even Hawaiian paniolo cowboys would hesitate to cross it. But the Golden Bear and his team didn’t hesitate to tame it. The stark contrast between verdant golf course and neighboring wasteland shows what a vivid imagination and a bold designer can do when he’s given a lot of money to work with. The Challenge is just such a course.

Two adjacent holes, Nos. 12 and 17, twist along the surf of the Pacific, They are among the most visually spectacular in all of golf. It’s no wonder Bill Gates chose to get married on this chunk of paradise.

The par-3, 12th is a forced carry across a chasm of Pacific to a clifftop green. Go ahead – hit as many balls as it takes to reach the green from the back tees 202 yards away. You’re likely to find a dozen abandoned balls in the grasses on the next hole, another par-3 where short hitters pull their shots left but are too stunned by the last hole to retrieve their runaway balls.

The 17th also requires you to blast a tee shot across the water, but the landing zone is deep and wide, more intimidating than risky.

Doug Stephenson, the director of golf for both Four Seasons courses, calls Challenge “the perfect resort course.”

“Its fairways are generous, the tee boxes offer an ideal balance of risk and reward for both men and women, and the course is forgiving off the tee,” he said.

While the ocean views from the Challenge will continually remind you you’re in Hawaii, the Experience will have you asking yourself if you’ve somehow changed continents.

The Experience at Koele is an inland course, rising and falling through wooded ravines thick with pines, koa and eucalyptus. Greg Norman and Ted Robinson designed the high ridgeline course, which takes full advantage of elevation changes and sweeping views of nearby Maui and Molokai. Keole is tight. Its strong par 3s and long par 5s are difficult to reach in two shots. Its cool, upcountry location near the center of the island keeps ambient temperatures 10 to 20 degrees cooler than at its sibling, the oceanside Challenge at Manele, which means bentgrass greens, a rarity in Hawaii, thrive on the Experience.

Those cool temperatures and occasional afternoon showers combine to create a lush, tropical background for pristine playing conditions. And there’s plenty of natural beauty to see.

“You play this course across hills and valleys lined with 25-year-old Cook Pines and ironwoods,” Stephenson told me during a recent round together. “It feels like you’re deep in a jungle. Then you come on to the 12th fairway and catch a view of the ocean. That’s when you realize you’re only a mile away from the beach.”

As we reach the 444-yard, par-4 17th, Stephenson pulls out a hybrid and whacks a drive to the edge of the green 250 feet below us. “I prefer the Experience a bit better than the Challenge,” he tells me. “It’s more difficult, the temperature is cooler and the views are the best on the island.”

Our round easily finishes in less than four hours, even though we were sandwiched between two couples; he was playing, she was reading and taking pictures.

“No wife is going to let her husband go to Lanai to play golf without taking her, so we’ve got to offer luxurious activities for her, too,” Stephenson explained. “We don’t charge a rider’s fee, we give the non-golfing spouse a few magazines, and we set them up with early morning tee times so they can be at the pool by noon.”

The Experience backs up to the Koele hotel, a low-slung plantation house styled like an elegant hunting lodge. Though you won’t find a beach, you will find horseback riding, croquet, tennis, hiking and sporting clay shooting. Nearby is Lanai City’s town center, a smattering of tiny shops, a library, the cultural center, and a small grocery store whose shelves grow bare if inclement weather prevents the weekly container ship from docking each Thursday.

Whether you lose yourself at the Four Seasons Lodge at Koele or Manele Bay, Lanai is the kind of Hawaii you don’t see anymore but that you dream about.

You can rent a Jeep at the island’s sole rental agency, fill it with fuel next door at the only gas station in town, then hike across the street to Coffee Works, at the far end of Dole Park, where you can sip a cup of fresh coffee under a billowy green awning while Journey plays on an endless loop. Hop in your Jeep, and you’re speeding off across the open land of Lanai to explore the nooks and crannies of an island you’ll think you have all to yourself.

Strangers will wave to you as you pass on the road – and even offer assistance if they see you struggling with your Jeep.

And if you’re a golf nut like me, here’s another golden key: you can bump up your green fee to a day of unlimited golf on both Four Seasons courses for just $50. “Just tell us you read about it in AVIDGOLFER,” Stephenson said.