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

Archaeologists say Hawaii was one of the last places on earth to be settled, probably around a.d. 900 by Polynesians sailing north from the Marquesa Islands in double-hulled voyaging canoes. When the first European, James Cook, arrived in 1778 – blundering into the islands much as my father had – he was greeted as a god, but soon wore out his welcome; an irate mob backed him into the waves in Kealakekua Bay, a few miles south of present-day Kona, and ran him through with a spear.

Randy and I hoped for a slightly better reception when we hopped a puddle-jumper over to the Big Island from Maui. Kona today is a distressingly generic place – box stores and strip development – but Chris Huber, a bike shop owner and former Coors Light team racer who set us up with mountain bikes, told us that beneath the placid exterior lurked plenty of tension. He had had car parts stolen, has been hassled while out riding, and in general was used to getting "big stink-eye."

We took a day to dry our gear and restock. At Wal-Mart Randy bought flip-flops and, perhaps hoping to attract some stink-eye himself, a floppy Panama Jack hat. That night we stole some milk crates from behind a Safeway to serve as makeshift panniers. Thus equipped, we launched south on Highway 11, the Hawaii Belt Road. It wasn't quite the cruiser route I'd been hoping for. The climbs were grinding, the heat unrelenting, and the "vog" – a kind of volcanic haze peculiar to the Kona coast – dispiriting. But at Captain Cook we turned off the Belt Road and plunged down to Kealakekua Bay, and suddenly Hawaii was beautiful again.

Swimming off the dock of the bay we met a group of schoolkids speaking a strange, mellifluous language: Hawaiian. Their teacher, Kalani Soller, an amiable 37-year-old with impressive Polynesian-style tattoos on his arms and legs, told us they were from Kau, on the windward side of the island, one of the last pockets of traditional culture on the Big Island. Soller pointed out the monument across the bay marking the spot where Cook had died. "It's kind of a joke we have with other Polynesians," he said. "Hey, you didn't take care of the guy, so we did." He smiled, then grew wistful. "He should have kept going and never stopped here."

We got as far as Hookena, where there's a little county park on the beach. That morning's newspaper had called Hawaii's homeless problem the fourth-worst in the country; looking around at our ragged fellow campers it wasn't hard to believe. A guy who called himself Pugsley came by to bum a smoke. "I need to get a job tomorrow," he said, eyeing the microwave burritos we were reheating on the stove.

"They're hiring at the Subway in Kona," Randy said helpfully.

"Nah, I'm into woofing," Pugsley said. "Working on organic farms."

Fires sprung up on the beach, and the smell of pot wafted through the palms. A hapless security guard made the rounds, attempting to collect campsite fees.

"I don't pay," our neighbor said. "Why should I? Everywhere I am is the Hawaiian kingdom."

She was a sovereignty activist, an advocate for the idea of Hawaiian independence, and she delivered a long but entirely coherent explanation of how the Hawaiian monarchy had been overthrown by the United States in 1893, and why it now needed to be returned to its rightful owners, the native Hawaiians, who, according to the U.S. Census Bureau, comprise about 10 percent of the state's 1.2 million people. (She was not some lone freak; I'd heard much the same story from my uncle, a retired corporate lawyer who now lives on Maui. "Legally, the case is strong," he told me.)

At midnight Pugsley reappeared with glazed eyes and a warning about centipedes. "Hawaiian snakes, man," he said. "The brown ones hurt, but the blue ones hurt so bad you'll hallucinate."

"Thanks for that," said Randy, who didn't sleep the rest of the night.

In 1778, a few weeks before Cook's death, one of his marines, an American named John Ledyard, tried to climb Mauna Loa. Starting from Kealakekua Bay, his small party made it about 25 miles up the mountainside before a trailless forest and a lack of water stopped them.

I suspect that for Ledyard, as for me, it wasn't about "conquering" Mauna Loa, or even wanting a good story to tell. It was something much more primal, an almost physical need to feel the mass of the mountain beneath one's feet and to reach its tantalizing, unlikely, snowcapped peak.

But our plan was better than Ledyard's. Rather than take a direct frontal approach, we would spiral around to the wet side of the island by bike, using a national park road to get about halfway up the volcano's northeast ridge, and then hike the rest of the way to the summit.

The first day, starting from the beach below Naalehu, was a Tour de France-scale climb of 4,000 vertical feet – except that we weren't on 16-pound bikes. More like 10 pounds heavier. It was raining and Randy suffered big-time, riding the last five miles, after dark, in the back of a pickup truck.

Day two was even bigger. After a punishing 2,600 vertical feet on the bikes to the Mauna Loa trailhead, we still had another 3,400 to go. Darkness overtook us on the lava flows, and our lone headlamp was failing (until we replaced the batteries). When we finally got to Red Hill Cabin, elevation 10,000, the temperature was in the 20s. Miraculously, there were blankets.

I went to the summit alone the next day. All of Randy's clothes were soaked, and the ranger who'd issued us a backcountry permit had made a point of recounting hypothermia horror stories. It was 12.5 miles each way – pretty much a full marathon, at altitude, through a wilderness of lava and steaming cinder cones. At 12,000 feet I hit the snow. By the lip of the caldera, at 13,000 feet, it was six inches deep. I worked my way around the north side of the bowl and followed a series of snow-covered ahu, or cairns, to the summit, a giant ahu perched on the lip of the caldera's western wall.

Clouds smothered the peak; I couldn't see much more than the caldera floor, a black expanse of twisted lava pocked here and there by steaming vents. The big views came on the way down, when the clouds lifted and the setting sun illuminated the snowcapped summit cone of Mauna Kea, 30 miles away across the saddle of the Big Island. There were a half dozen structures clustered there, astronomical observatories, relay towers, and the like, and they made me somehow angry. Squatting on that great summit, they seemed sacrilegious – and by extension so did the whole idea of developing these islands for our 21st-century purposes. But what was the alternative? Independence or not, there was no turning back the clock.

For days we had been anticipating the last leg of our trip, the long descent to Hilo and the sea: 38 miles of pure downhill bliss. For the first two miles that's what it was. Grinning like idiots we zinged down the side of the volcano, ghostly ohia trees flicking by overhead. Then Randy pulled up. "Check out my back wheel," he said, shaking his head. "It doesn't feel right."

That was understating things. His tire was self-destructing under the load. We had no spare, not even any duct tape. We MacGyvered a fix, lashing parachute cord around the rim, but that meant the rear brake had to be disengaged. Randy lowered his seat and set off, flip-flops scraping the road like Barney Rubble brake pads.

Four miles later I got my first flat of the trip; a mile later, my second. Huber had supplied us with a handful of CO2 cartridges in Kona, assuring us they were better than a pump. Now they were all gone. I crept down the hill with exaggerated caution, but it was no use, and within a mile I flatted again.

I suppose I could have ignored the rental car that inevitably appeared, a hideous Chevy HHR, and the offer of a ride from its occupants, a very nice couple from Santa Fe. But pride has its limits, so I threw my bike in the back and hopped in. A mile before the Belt Road we caught up with Randy, staring mournfully at the shredded remains of his tire. With limited space in the car we decided to lock the bikes to a post and go have some mai tais in Hilo.

In the end, there was only one way to get the bikes back and still make our plane. As I signed for an electric-blue HHR of our own, I was amused to see that it cost less per day than the two bikes did. I can't deny that it was awfully nice to have a motor other than our own zipping us back up that 38-mile hill, with beer-holders on the console and a decent sound system to boot. It's just that after a while, it was kind of hard to tell if we were still in Hawaii.