Fifteen. That’s the number of times I’ve counted my guide, Marcom Pascua, wave hello to a passing vehicle.

He’s the co-founder of Lanai Cycles and we’re biking across the length of this island he calls home. Every car, pickup truck and hotel shuttle that breezes past us while we cruise along its wide open roads is greeted by his friendly open palm and, every single time, its driver reciprocates the gesture without missing a beat.

“I actually forget I do that sometimes!” Pascua shouts into the open air rushing between us on Kaumalapau Highway as he leads me down this main expressway lined with tall, scenic Cook pine. “It’s, like, second nature!”

The author and guide's bikes perched at

the start of tour just as the fog rolled in.

I hadn’t commented about these endearing drive-by salutations, but he feels the need to acknowledge the quirk anyway, recognizing that even for someone like me, born and raised on the streets of Oahu where waving mahalo (thank you) when someone lets you in their lane is the norm, the friendliness of the highways here is on another level.

“People come here just for that,” Pascua says of the island’s way of living, a place with just a single modern-day settlement, Lanai City, where the majority of its 3,200 populace resides. “They want to see the one gas station, the one school, the one poke shop. When I tell people my graduating class had about 30 kids, they trip out.” It’s a deep sense of community you can really feel everywhere, and that I’ve been tallying these clockwork exchanges in place of mile markers is one of the more notable reminders we’re not biking in just any part of Hawaii; we’re biking on Lanai—the perfect place to slip into an endless 15-mile cruise control. After all, Lanai doesn’t have a single stoplight.

It was 8 a.m. when we first kicked off our three-hour sunrise ride from the top of Keomuku Highway, a start point situated 2,000 feet above sea level along the island’s Koloiki Ridge. The tour, which is all downhill, is divided into two halves: the east and west side, with a quick pit stop through historic Lanai City in between. It’s the standard option offered by Lanai Cycles, a relatively new bicycling excursion co-owned by Pascua and part-time Lanai resident, Jeremiah Littlepage, that asks visitors to go slightly against the grain of the island’s practiced travel narrative: trade in your four-wheel-drive Jeeps, the de facto rental for exploring its terrain, for a slimmer pair of two (or at least for the morning, anyway). It’s also partly family run; Pascua’s mom, Auntie Helen, casts herself as our chauffeur today, waiting for us at the bottom of both highways in a pickup truck to transport us and our bikes back to Lanai City.

Along Keomuku Road. Photo courtesy Lanai Cycles

We strapped on our helmets and Pascua gave me a quick briefing of my ride’s bells and whistles—Lanai Cycles runs on Specialized Sirrus multi-use road bikes, a model designed for everyday townie riding—while a thick fog surrounded us, remnants of a gusty, pre-dawn rainstorm. It nearly cancelled our tour hours earlier, but Pascua ensured me he scoped out the roads beforehand to verify its safety and that once we reach mid-descent the visibility will clear up.

And he was right. Keomuku is smooth and curvy, the highway playfully disappearing behind red dirt hills as if to suggest a game of hide-and-seek, when a sweeping panoramic view of Maui and Molokai reveals itself. Pascua rides a fair distance ahead of me, the silhouette of his neon yellow windbreaker nestled between the two neighboring islands in the distance, and I find my feet leaning on the brakes to take it in: the slopes of Haleakala across the Auau Channel to the right, the deep ridges of eastern Molokai's mountains stretching out into the Kalohi Channel to the left.

“It feels brand new for me every time. You can’t beat it,” Pascua says, after we pull over to a lookout at the side of the road. “We try to time it so that when we reach this exact spot, we can pause, drink coffee, eat pastries and fruits from the city, just after the first light is peeking out. Especially this time of year, with the sun coming up over Haleakala …” he trails off, letting the natural scenery fill in the blanks. Below us, the remainder of Keomuku zigzags down to an 8-mile stretch of beach called Kaiolohia, nicknamed Shipwreck Beach for two sunken vessels off its shores, one of which, the World War II Liberty, can be made out from this vantage point.

On Lanai, Pascua’s hand motions over Maunalei Gulch, a thick forest trench to our right that narrows alongside the road to the ocean. “This gulch is one of the most ancient and culturally significant to Hawaiians on the island,” he says, as someone who’s hiked into it many times. The earliest native settlers cultivated it as a source of irrigation for the region and farmed kalo (taro) in it. “It’s such a beautiful place, so much mana (spiritual power) inside, as soon as you walk in you can feel …” his voice hangs suspended in the air again. “You can just feel everything down there.”

Riding down to the coast with Molokai in the distance. Photo courtesy Lanai Cycles

At that moment, a Jeep full of visitors (because only nonresidents drive these shiny models around Lanai) darts past us and I kind of feel bad for them. They don’t have someone like Pascua to share with them this intimate knowledge, sides of the island I surely would’ve raced past also. On a hillside slant above Maunalei, an axis deer prances across the terrain. Following its graceful lead, we decide to get going also and push back onto the pavement.

On the leeward side of Lanai, the vibe is dramatically different, the most in-your-face apparent being the climate—drier and hotter, as evidenced by the sweat perspiring down my neck—and landscape, a wide open expanse of mustard yellow hills that unfurl out to Kaena’s sea cliffs, the island’s westernmost point. Then there’s the water. The way the nearing-noon sun fiercely hits the ocean sparks a blue so dazzling I’m convinced Pantone should name a shade after it.

The west side is also a more exhilarating downhill ride. Kaumalapau Highway is less traveled, soothingly spacious and with more sprawling curves. Cruising behind Pascua as we coast around one of them, we dip into a sudden wind tunnel. I grip my handlebars tight and keep my head low, literally bowing before the curative powers of Lāna‘i’s landscape and its surprising ability to catch you off guard just as you think you’re settling into it.

The end of the tour: the breakwater at Kaumalapau Harbor.

At the base of the highway we reach Kaumalapau Harbor, the main commercial seaport of Lanai. It houses an idiosyncratic breakwater—more than 800 stark white, 35-ton concrete armored units piled atop each other—that impressively is the largest of its kind in the world. As Pascua and I park our bikes and hop onto the breakwall, I run through a mental list of all the places he mentioned I still want to go back and explore deeper: the Munro Trail; Lanaihale, the island’s highest peak; and of course, that poke shop in Lanai City. Standing on the stone wall’s furthest point, it marks the end of our bike tour, but the beginning of even more adventures this island has to offer.

Lanai Cycles • $180 per biker, must be at least 12 years old and have experience riding a bicycle, no beginners. • (808) 563-0535, lanaicycles.com