Tracing the island’s edge on winding Highway 30—the Maui Loop—Andrew McCarthy finds history lurking at every turn.
Credit: Joe Schmelzer

For 10 years I lived on the Hawaiian island of Maui. I had a complex relationship with paradise.

When I stood in my backyard and looked off across Maalaea Bay, the West Maui Mountains dominated my view. The mountains, carved from half of the volcanic doublet that comprises the island, are encircled by a road embracing two sides of Maui that live in sometimes uneasy alliance: the tourist-bloated Maui for which I have both a snobbish aversion and an abiding affection, and the more local island—the almost “underground” island I love and yet would never be fully a part of. Highway 30 plunges me into the paradox of Maui. It lets me know I’m back.

Since 30 is a 60-mile loop (with a treacherous section still named County Road 340), you can pick it up anywhere along the line, and I slide into its quick-moving flow just before Maalaea, a small community on the isthmus between Haleakala, the 10,000-foot cone that presides over Maui, and the shield volcano that created the West Maui Mountains.

The road begins to climb, and Maalaea Bay, home to humpback whales during the birthing season of November through May, sits off to my left. The Pacific will hug my shoulder, while the West Mauis—which at this point appear dry and brown, more large hills than sacred mountains—will weigh heavily on my right for my entire trip as I move clockwise around the island.

Offshore, Kahoolawe, the uninhabited island that was used until 1990 for target practice by the Navy, rises up. The road swoops on. The island of Lanai, once devoted almost entirely to pineapple production and now home to a few posh resorts, slips into view. The ever-changing perspective of the neighboring islands informs a sense of distance traveled that might otherwise go undetected by simply gazing out onto a vast expanse of ocean.

I pass into a tunnel blasted through rock and honk my horn, this being a local superstition that is said to ward off evil spirits (who knows, but I’d never consider not honking, and neither would the several cars I pass inside—the sounds reverberate). The road settles down to sea level, and a small sign catches my eye: the valley isle sport shooters club. I double back.

Not far up an unpaved road I come upon a group of about two dozen men armed with large pistols, multiple clips of ammunition strapped to their belts. They regard an obvious interloper with caution, but continue about their business; a shooting competition is about to get under way. Ray, a Maui native, shows me his equipment with pride—a modified 9-millimeter pistol and a number of bulging clips of ammunition. “I prefer the hollow tip. See.” He thrusts a bullet under my nose for inspection: “It keeps the gun cleaner.” Without comprehension of why that might be, I nod my admiration and wish him luck in the day’s event. The sound of gunfire and the ping of bullets on metal targets is lost in the trade winds as I head back toward the young families playing on the beach a few hundred yards—and a world—away.

A little farther on, the West Mauis, rising 5,788 feet, take on imposing dimensions. Deep, lush green valleys are visible amid jagged drop-offs. The nearly impenetrable mountains were home to the last great battle for dominance on Maui (in the Iao Valley), and perhaps because so much of their interior remains inaccessible, they exude a sense of inviting and forbidding mystery.

And then suddenly I am in Lahaina, the most energized and enervating town on Maui. It’s a place where you can have your picture taken on the street with multicolored parrots perched on your person, or you can spend $1,400 on a ukulele made of curly koa wood. You can buy art by Picasso, or Chagall, or Dalí, and then step next door and have a beer at Moose McGillycuddy’s Pub.

It’s easy to dismiss Lahaina (which translates as “merciless sun,” and it always feels that way) as a tourist-riddled sham, and the longer I walk down Front Street, passing scores of men and women in floral clothing, the closer I am to doing just that. But Lahaina is also a town rich in well-preserved history, a history that juggled the relationship between the whaling industry and the missionaries during their heyday in the mid 1800’s. From a look at the records available in the old prison, Hale Paahao (“stuck-in-irons house”), built by King Kamehameha III to detain unruly sailors who refused to return to their ships by sundown, it’s easy to see which group prevailed more often than not. In 1855 there were 330 convictions for “drunkenness” and 169 for “fornication,” as well as 89 for “furious riding.” But apparently life in the prison, which is beautifully preserved, with its well-manicured yard under large monkeypod trees just off the main drag, was not all bad. Seaman William Mitchell Stetson confided in his diary: “Male and female all had freedom of the prison yard and mingled promiscuously.” And if the hardships of jail life ever did become too much of a strain, the wooden cells were barely secure and the coral restraining wall, at just over 10 feet high, was easily scaled once the sailors sobered up.

With Lahaina in my rearview mirror, I am swallowed in Kaanapali, created in the 1960’s as Hawaii’s first planned resort area. Its beautiful stretch of beach is blanketed with one hotel and condominium after the next. Many never venture beyond the grounds, but what I’ve come to see isn’t drawing much of a crowd. Tucked deep into the back corner of a shopping mall, past the Tommy Bahama and Coach shops, sits the tiny, well-laid-out Whalers Village Museum. The history of whaling is both a testament to American can-do and a shame worn uneasily. As I wander through, reading the young sailors’ stories—many were teenagers who couldn’t even swim—and looking at the harpoons and killing irons, a mother awkwardly tries to explain to her young daughter (they are the only other visitors) exactly what the point was, and why the leviathans were driven to near extinction before whaling played itself out in the Pacific by the 1870’s.

Farther up the coast, the insular island of Molokai, famous for its leper colony, hovers close offshore. Inland, tall ironwood trees announce Kapalua, 23,000 acres of Maui’s most well-thought-out resort development, which includes a recently renovated Ritz-Carlton hotel.

And then it all stops.

No more resorts, no more condos, no more shops, no more houses. The island reasserts itself and the road is forced to narrow. Trees are bent and twisted from wind that seems unimaginable on this still day. The baking sun, coupled with the lunar-like lava beginning to dominate the terrain, starts to addle my mind. I pull off and hustle down a lava-rock path. A quick swim in secluded Honolua Bay, a close encounter with a very large sea turtle, and I am refreshed and back on the road.

On this back side of the island, the West Maui Mountains exert themselves and push the road around like a piece of string, tight switchbacks yield to long swooping arcs that bring me deep into valleys and then shove me back out toward the coast. My radio is filled with static. My phone has no reception. I pass a sign that reads narrow winding road. “No shit,” I say aloud, and turn the wheel hard, left hand over right. I pull off and look out into the endless Pacific—no more islands in view here, just open sea for thousands of miles. I breathe deeply. Probably the cleanest air I have tasted in … ever.

The double yellow line that has been my guide is gone now, replaced by a faded, intermittent dash in a road that has withered even further. The pavement has begun to buckle under in spots. Highway 30 has morphed into County Road 340. Up ahead, at the apex of a switchback, I see a young man sitting alone in a folding chair, miles from anywhere. I approach and he smiles loosely and calls out, “Buds … Maui buds.” He gestures—forefinger and thumb pinched together, rising to his mouth. I drive on. The road becomes so narrow that leaves brush my car on both sides. A sign tells me the speed limit is 25 mph—that is wildly optimistic. If someone comes around this bend in the road, one of us is going to have to do some fancy reversing for some distance.

And then, like an oasis, Kahakuloa comes into view beneath me. Nestled in a small valley on a black-rock beach, it’s a settlement of roughly a hundred Hawaiians. Maui the way it used to be, insular and slow. Moana Coston is the youngest of eight, and she’s selling her Auntie Julia’s homemade banana bread from a roadside stand. “It’s nice here in the valley,” she tells me vaguely, glancing off. I ask if she has ever left. “I did. It wasn’t for me. I came back.” She has a wide, easy smile. “I was on Oahu for a year. Too fast,” she explains.

“Think you’ll ever leave again?” I wonder.

“Might be nice to marry someday.”

“Someone from the village?”

Coston laughs wildly, surprisingly: “No way. I see them every day, I know everything about them all.”

Beyond Kahakuloa, impossibly, the road gets even more treacherous. I’m giddy as I round blind, one-lane curves with sheer mountain walls on one side and plummeting drop-offs with no guardrail on the other. And then the road takes a hill and the land opens, and without warning I’m in grazing country: I swear I could be in Connemara, in Ireland.

Eventually, the northern slope of Haleakala comes into view and civilization is not far off. Feelings of relief mingle with disappointment. It’s all downhill, and the road dumps me into Wailuku, the county seat with a worn-out charm.

I settle in at a vinyl padded booth and Formica table for the best bowl of pho on the islands, in the most local of local haunts—Jennifer Nguyen’s Saigon Café. And then I’m back on Highway 30. Instead of carrying on just the few miles that will complete my loop drive, I find myself turning right, onto the only road that leads up into the West Maui Mountains, into the Iao Valley—the burying place of royalty. It’s a spot that is at once sacred Hawaiian land and tourist hub, and one of the best examples of a harmonious marrying of the two disparate—sacred and profane—aspects of the island. With valley walls engulfing me, the hanging sun struggling to penetrate the loitering clouds, the road quits at a parking area. I leave my car and step out into the heart of Maui.

Fly into Maui’s Kahului International Airport. For car rentals, book ahead on or to get optimal rates.


Great Value Kaanapali Beach Hotel The 432-room low-rise hotel comes with authentic Hawaiian atmosphere, thanks to activities such as lei making. 2525 Kaanapali Pkwy.; 800/262-8450;; doubles from $159.

Ritz-Carlton, Kapalua More than 460 remodeled rooms, an elaborate spa, and a Jean-Michel Cousteau environmental excursion program, all at a resort with a century-old pineapple plantation. 1 Ritz-Carlton Dr.; 800/241-3333;; doubles from $299.

Great Value Royal Lahaina Resort Set on 27 acres, many of the recently renovated cottages have ocean views. 2780 Kekaa Dr., Lahaina; 800/222-5642;; doubles from $165.


Aloha Mixed Plate 1285 Front St., Lahaina; 808/661-3322; dinner for two $36.

Julia’s Best Banana Bread 7465 Kahekili Hwy., Wailuku; 808/242-4399; dessert for two $10.

Moose McGillycuddy’s Pub & Café 844 Front St., Lahaina; 808/667-7758; dinner for two $20.

Saigon Café 1792 Main St., Wailuku; 808/243-9560; dinner for two $30.

See and Do

Hale Paahao (Stuck-in-Irons House) Corner of Prison and Wainee Sts., Lahaina; 808/667-1985.

Valley Isle Sport Shooters Hwy. 30, Lahaina; 808/269-5543;

Whalers Village Museum 2345 Kaanapali Pkwy., Kaanapali; 808/661-5992;

Tour Operators

Hike Maui A variety of half- and full-day excursions are led by one of 15 experienced Maui guides. 285 Hukilike St., Kahului; 808/879-5270;; tours from $75.

Maui Ecoventures For custom trips or guided day hikes of Maui’s rain forests and villages. 180 Dickenson St., Lahaina; 808/661-7720;; tours from $80.