Crossing Hawaii's Biggest Islands
Credit: Chris Clor / Getty Images

When I was 15 my family sailed from Santa Cruz, California, to Hawaii. Fourteen days out my father, who was navigating with a sextant, announced that we had another 500 miles to go. So it was something of a surprise when the cloud-wreathed mass of Haleakala Crater, the dormant volcano that forms the eastern half of Maui, reared up out of the sea the very next day. For me the real shock was the exhilarating upsweep of those high green islands, like someplace I'd imagined but never seen yet.

Clearly I'm not the only one Hawaii has seduced. More than 7 million people visit the place every year. Wide-bodied jets from the mainland fly nonstop to four islands now, and the state's hotel occupancy rates are second only to New York City's among U.S. destinations. It's hard to get away from it; round a corner on a wild coast road and, sure enough, there's another pale face, what the native Hawaiians call a haole, in a shiny Dodge Neon coming the other way.

I didn't want to be the haole in the rental car; I wanted to get off the path and see a less packaged, more primeval place, the raw Hawaii that geologists say is still emerging, eruption by eruption, from a "hot spot" in the middle of the Pacific plate. So on New Year's Day I flew to Hawaii with my friend Randy Harris, a wicked hangover, and an ambitious plan to traverse the two youngest, largest Hawaiian islands. We would cross Maui on foot and circle Hawaii, also known as the Big Island, by bike, topping out on two of the island chain's three major volcanoes. Except for a bit of thumbing on day one, it was going to be human power all the way.

It made sense to start on the far east side of Maui, where Haleakala drops down to an untrafficked, Edenic coast. Haleakala would be a warm-up for our ultimate destination: the Big Island's still-active Mauna Loa, a 30,000-foot seafloor volcano that may be the biggest mountain, base to peak, in the world. Of course, only the top 13,600 feet protrude above sea level, but that's enough for it and its virtual twin, Mauna Kea, to draw the occasional wintertime blanketing of snow.

Hawaiian snow! I didn't know why the idea drew me so powerfully, but I wanted to be there when it happened, to crunch around and feel firsthand the power of a place that, smack in the middle of the Pacific Ocean and a mere 20 degrees north of the equator, could nevertheless reach so high as to call down that kind of a blessing upon itself.

That first morning, though, our plan to escape the haole hordes didn't go so well. Lacking a vehicle and short on time, we'd planned to hitchhike the first leg, the 37-mile Haleakala Highway, which climbs from sea level to 10,000 feet. The only problem was that nobody stopped. "Wow," said Randy, as the sun climbed higher and we began to roast. "This kinda sucks."

We'd reached the point of despair when a kid named Ryan pulled over in a big flatbed loaded with plastic bins. There was no public recycling on Maui, he explained; he was a private hauler heading up the volcano to pick up Willie Nelson's empty beer bottles. "But hey," he pointed out, "at least we're burning biodiesel."

On the way up, Ryan gave us a different view of Hawaii from the tourist board's. He said there was a distinct anti-haole vibe in Kihei, where he lived. More than a vibe. Local kids threw rocks at tourists if they drove down the wrong street. That was old hat in Hawaii, of course, where massive development seems not to have done much for the descendants of the original inhabitants, and resentment consequently runs deep. A new wrinkle, he said, was the ice problem: crystal meth. Surprisingly, it wasn't young people who fell prey so much as 30- and 40-somethings, "people with no jobs or dead-end jobs."

Ryan blew right past Willie Nelson's homestead and took us all the way to the National Park entrance gate at 7,000 feet. We got out and stretched in the now cool air, breathing in the pure oxygen of the trade winds. A rainbow broke over the flank of the volcano, and for a moment there, it felt almost like old Hawaii. Then a fat-tired train of "downhill cruisers" came tootling by, in absurd full-face crash helmets and matching light-blue windbreakers and windpants. At the head of the line their guide put his hand up – not waving to us but telling his charges to slow down.

From the parking lot at the end of the highway it's about 10 steps to the glass-walled observation platform that squats on Haleakala's summit. Inside, shivering, underdressed women clung to their boyfriends and peered down into the gaping, Manhattan-size crater – actually a mountain ridge blown open on two sides by eruptions. Outside, Randy staggered around trying to take pictures of a ranger holding a wind gauge (gusts to 54 mph, he told us). Randy's pale New England skin was already turning an alarming shade of pink, as he'd neglected to bring a hat, sunglasses, or sunscreen, and the sole of one of his shoes was falling off. "Uh, do you have any strapping tape?" he'd asked earlier that morning at the park entrance station. The ranger there, who'd just finished grilling us on our backcountry expertise, eyed him coolly. "Sure," he drawled. "On the cinders, it should last about 20 minutes."

I wasn't worried. The apparent chaos was all part of Randy's MO, and you couldn't argue with the results. Within a few minutes of heading down the crater trail he was shooting a beautiful Swiss tourist as she slathered her arms with sunscreen. An hour later he was at it again, persuading a stylish Russian day-hiker to paint herself with a vermilion-colored stone.

That night, after a 10-mile hike through an alien landscape of red and black lava flows, towering cinder cones, and "groves" of a tall, gray-green lobelia-like plant known as silversword, we camped under the crater's steep western escarpment. I pulled on all my clothes, climbed into a fleece sleeping bag liner, and still froze. The next day we set out to climb Hanakauhi, a great triangular peak on the far side of the crater. Woozy from too much sun, Randy bailed halfway up. I topped out after a long, satisfying scramble along the airy summit ridge. A tourist helicopter clattered past, then circled back for a second look.

We stumbled down the Kaupo Gap the next day, thighs cramping and toenails dying as we dropped 6,400 feet through every conceivable microclimate on the planet. Silversword gave way to scrub; then came ferns and cloud forests, home to the last few native Hawaiian birds. (The mongoose, brought in to control the cane rats, wiped out most of the island's birds as well.) Finally we were out of the park and walking through eucalyptus groves and a cattle ranch, toward the whitecaps of the Alenuihaha Channel. Resting at a water tank, we met a Hawaiian cowboy named Peter, a beefy guy in a camo jacket riding an ATV. He'd moved to Kaupo, population 40, a couple of years earlier.

"I can't take it over on that side no more," he said, gesturing in the direction of Kahului, Maui's main city.

"A little too whited-out?" Randy asked.

"You got that right. All those airplanes, one after the other."

Even if we'd wanted to drive the last 16 miles to Hana, on Maui's eastern tip, we couldn't have. There had been a big earthquake in October, and the road from Kaupo, the only road around the south side of the island, was closed even to foot traffic. We stepped over the roadblock and saw why. Several huge boulders had fallen from the cliffs above the roadway, pulverizing the guardrail. We picked our way carefully beneath the overhangs at first, then just went for it in one full-on sprint, laughing like maniacs to hide the fact that we were scared shitless.

Safe on the far side, we grinned as couples in new Mustangs and Jeep Wranglers stared forlornly at the road closed sign. To get back to the condos and hotels of West Maui, they were looking at a U-turn and a four-hour reprise of the infamously twisty Hana Highway. "You mean there's no other road?" one woman asked plaintively, as if it were our fault.