From the wheel of the big four-wheel-drive Suburban, our guide nods at a small roadside sign pointing to a beach called Lapaiki.
"That's one of those dotted-line roads on the map," he says. "If you go down there you might as well be driving up and down flights of stairs."
In other words, roads can get rough on Lanai.
As it is, navigating the deeply grooved road we're on, leading through ironwood-crowded Kanepuu Preserve to a rocky landmark known as the Garden of the Gods, is a bit like driving down an oversized bowling-lane gutter carved in red dirt.
Good luck here on one of those days when Lanai gets some of its 15 to 20 inches of annual rainfall.
That's why four-wheel drive is the standard for vehicles on back roads of what's historically been known as the Pineapple Island, where a 20,000-acre Dole plantation once grew 75 per cent of the world's supply of the fruit.
That changed in the early 1990s when labour prices moved the pineapple industry to Southeast Asia, Mexico and South America.
Lanai ploughed under its fields.
Today, besides the company town of Lanai City, the main reminder of the Dole days protrudes from dirt along some of these back roads: myriad bits of black plastic, remnants of sheets laid down to retain moisture in the pineapple fields.
Now, fields have gone to wild grasses and brush such as the invasive (and toxic) Brazilian pepper plant.
For 20 years, Lanai has struggled to reinvent itself, but now the game is on.
Just over a year ago, Oracle software billionaire Larry Ellison bought 98 per cent of the island from another billionaire, Dole Foods CEO David Murdock and his Castle & Cooke Co., for an estimated US$300 million-plus. (State and local government and individual homeowners hold the other 2 per cent.)
Ellison, No 5 on Forbes' list of the world's richest people, has big plans for the little island.
So far, for tourists the most obvious signs of new ownership are (A) higher rates at the island's two resorts (around US$660 a night for an ocean-view room at the Four Seasons Manele Bay), and (B) attractive new landscaping of heliconia, bird of paradise and other tropical plants in front of businesses around Lanai City.
"The former owner didn't want the town to be a place visitors wanted to stay. He wanted them at the resorts, so he didn't make the town a very nice place," said my guide, Honolulu-bred Bruce Harvey, who moved to Lanai in 1999.
"We're real happy Ellison is here."
The 141-square-mile isle has had its share of brushes with billionaires. Bill and Melinda Gates married here in 1994 and booked all of Lanai's rooms to ensure their privacy. (Gates, too, reportedly was interested in buying Lanai last year.)
For now, the glow of big bucks is just starting to rub off on Lanai, which is a 45-minute ride aboard a passenger ferry from Maui, making it an easy day trip.
The reason to visit isn't for exotic scenery - much of the island is barren scrub - but for a taste of laid-back island life from, say, 50 years ago. It is a close-knit community with modest, plantation-style homes and few tourists.
On an island with only about 3,000 residents, 30 miles of paved road and no traffic lights, drivers still wave as they pass.
Wednesdays are big because it's "Barge Day," when the weekly supply barge brings fresh groceries (such as US$9-a-gallon milk).
The sports teams for Lanai's high school (and primary, and middle school, all rolled into one) compete under the endearingly geeky names "Pinelads" and "Pinelasses."
"There are no drugs or vandalism, or homeless, here, so parks don't close overnight," Harvey told me. "For all practical purposes, we have a zero crime rate."
Almost all residents live in the grandly named but charmingly sleepy Lanai City.
Ellison won fans when one of his first acts was to reopen the community-swimming pool, closed seven years as a cost-cutting measure.
"The humble old community pool didn't just reopen, it was reinvented as something worthy of a five-star resort," Honolulu Magazine noted in its August issue.
Under the legacy of Dole's "company town," Ellison's ownership takes in pretty much everything, including almost a third of the housing stock.
He even owns Dole Park, a big rectangle of grass and towering Cook Island pines in the town's centre, and most business properties, such as the handful of restaurants, galleries, gift shops and markets fronting the park.
So when Ellison spruced up the place, people noticed. The park's pines got their first pruning in years. Picnic tables went in. A park pavilion got a new roof for the old men who pass their days there.
But that's just the start. Ellison's development company, led by a Lanai-born resort-management veteran, in July changed its name from Lanai Resorts to Pulama Lanai ("Pulama" is a Hawaiian term for "to cherish").
According to pulamalanai.com, the name reflects "the deep sense of stewardship we feel for the island and the spirit that will guide endeavours that reach far beyond our resorts" - those being the island's two Four Seasons resorts, part of the purchase.
Ellison's vision, the website says, is "to establish Lanai as an island powered by solar energy, where electric cars would replace gasoline-powered, and seawater would be transformed into fresh water and used to sustain a new organic-farming industry that would feed the island and supply produce for export."
- Growing premium-quality fruit such as mangos and pineapple for sale to Japan and other high-end markets.
- Adding a small new resort, with ultraluxury "grass huts on the beach," at Kahalepaloa, site of the defunct Club Lanai. Local planners have already given first approval.
- A 50-acre tennis academy.
- A base for racing yachts, reflecting Ellison's America's Cup interests.
- In keeping with the island's old-fashioned feel, a 1950s-style bowling alley and soda fountain.
And it's not just talk. To make it easier for visitors to come, Ellison has already bought one Hawaii airline, Island Air, and is closing on the purchase of another, go! Airlines. Plans are to extend the runway at Lanai's airport for bigger planes.
And to draw more high rollers, his team last December wooed a branch of Nobu, the luxury Japanese restaurant chain run by celebrity chef Nobu Matsuhisa, to the Four Seasons Manele Bay just in time for the holiday rush.
So once you're on Lanai, what's there to see?
That's the selling challenge.
For folks with money, the attraction has been the fancy resorts and golf courses - without the tourist crowds.
Others come to hunt axis deer and mouflon sheep, non-native species that have taken the run of the island. Lanai's natural beauty is more subtle.
Back in the big Suburban, Bruce Harvey tells us about the Garden of the Gods, or Keahiakawelo, a place of stark beauty with red rocks and lava formations carved by wind and weather. Legend says the rocks were dropped from the sky by gods tending their gardens.
In the distance broods the island of Molokai, beyond wind-tunnel-like Kalohi Channel.
"We call that the Tahiti Express, because if your boat motor conks out, that's where you end up," Harvey quips.
Navigating the lumpy roads feels like riding a lunar rover, and the landscape fits right in.
Across the island, Harvey shows us Shipwreck Beach, where the first recorded foundering was in 1824, when square-riggers couldn't tack against the wind and got trapped here.
To this day, the hulk of an abandoned Navy oiler rots in the waves.
Walking the quiet beach we find coral bits and puka shells by the handful.
Back in the car we ascend a hillside of scrubby trees and more red soil, where tropical forests prospered until 1778, when the king of Hawaii island invaded Maui and lost.
To save face, his war party landed on Lanai, consumed all the food, burned the forests and slaughtered thousands. Lanai never fully recovered.
Now Lanai has a new champion, a king of commerce with lofty dreams. Will the Pineapple Island achieve new greatness - or will that road, too, be rough? Wait and see.
IF YOU GO:
By air: Ellison-owned Island Air has five flights daily between Honolulu and Lanai.
By sea: Day trips from Lahaina are a popular add-on for Maui visitors, who make the 45-minute passage aboard the Expeditions passenger ferry, with five round-trips daily. US$30 ($36) each way for adults, US$20 ($24) for children. Warning: Seas can be rough, especially in the afternoon. go-lanai.com.
Expeditions also offers Lanai packages including golf, guided tours, Jeep rentals and more.
Dollar Rent-a-Car on Lanai rents Jeeps and, unlike most rental agencies, lets you drive on unpaved back roads (weather permitting).
Unless you book a tour, ferry passengers need to get a shuttle van to visit Lanai City, which is about 20 minutes from the dock; US$10 ($12) round-trip.
Two Four Seasons resorts, the Lodge at Koele and Four Seasons Manele Bay, are the primary options.
Also consider Hotel Lanai, built in 1923 by James Dole as lodging for his executives. The pristinely maintained 11-room inn exudes traditional island charm. Rooms start at US$145 ($175).
MUSEUM: The free-admission Lanai Culture & Heritage Centre tells the island's story. It's opposite Dole Park in Lanai City; closed Sunday.
TRAVELER'S TIP: Get a 6:45 am ferry from Lahaina for a crossing on calmer seas, and nab a decktop chair to see the sun rise over Maui mountains. Watch for whales in winter and spring.
MORE INFORMATION: gohawaii.com