Photo by James Brennan

Moloka‘i Itineraries

Moloka’i Off the Beaten Path

The Friendly Isle, the Most Hawaiian Islands, sleepy and contented

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Moloka‘i once played with big-time progress by installing a traffic light at its busiest intersection. When it broke, no one bothered to fix it, and no one has missed it since. Progress has been stepped up lately, though; the island got its first movie theater in 1997.

Chances are you’ll either fall in love with Moloka‘i or you’ll never return. You’ll wonder why the heck you ended up here or you’ll accept her distinct differences and sink into her spirit—her spirit that thrives on family, culture, and community. If you can find peace of mind anywhere, you’ll find it here—where no one honks their horns or hurries or utters pretenses. Honolulu is only 25 miles away, but you might as well be another country and century here. Decide to this charming island on its own terms or don’t bother.

Even though less than 60,000 visitors step foot on Moloka‘i annually, islanders are generally ambivalent about even that many outsiders. Resistance to conventional (or any) tourism efforts runs high. Change creeps at a glacial pace, barely perceptible. Because of that, the island is still basically undeveloped; no buildings are higher than a coconut tree. Preservation of traditional culture is revered. Perhaps not surprisingly, a higher percentage of Native Hawaiians (more than 50 percent) live here than on any of the other islands except Ni‘ihau.

Many of Molokai’s 7,400 residents farm, fish and hunt just enough to get by. You may see them casting nets into the water, fishing, collecting seaweed. You will definitely see them gathering with friends and family on Sunday—and come to think of it, on most days at sunset or at lunch, at the beach park or at the gas station.

Other than a scenic and stirring day trip to Kalaupapa, the island doesn’t offer a great deal of organized activities for visitors—which is not to say there’s nothing to do. There is just enough to explore on your own, from deserted beaches to sacred ruins. The East End offers a panoramic view of scenic Halawa Valley not to be missed, and the same can be said for the world’s highest sea cliffs. But mostly Moloka‘i is a place for offbeat adventuring. There’s horseback riding and mountain biking and a bit of kayaking. It’s the place to hike undisturbed in spectacular Nature Conservancy property. It harbors Hawai‘i’s highest waterfall.

Moloka‘i is a spot to slow down (thereby seeing more), step out of the mainstream of tourism, and absorb the spirit of an island that refuses to forget the Polynesian past.

Central Molokai

Moloka‘i has one “real” town, and that’s friendly Kaunakakai: the population and market center on the historic south coast, with Ala Malama its dusty and parched two-block shopping street. It’s worth spending a little time hanging around here and watching Moloka‘i’s world revolve. Aging wooden storefronts and pickup trucks give the town a Wild West sort of feeling.

Head north from here through plumeria trees, alongside a coffee plantation, and up through a cooler and wetter forest to a vantage point overlooking Kalaupapa, formed by a flat “spreading” of lava. (The rugged “back side” of Moloka‘i is basically inaccessible wilderness, and its famed sea cliffs are viewed only from the air and by experienced kayakers.) Today, Kalaupapa National Historical Park, where people with Hansen’s disease (leprosy) were once exiled, can only be visited on a guided tour.

The island was formed by two volcanoes: the 1,381-foot Maunaloa in the West End (dominated by dry ranchland and rolling pastures) and the 4,970-foot Kamakou in the East End (shadowed by misty and lush rain forests). A single two-lane road runs the length of the island.

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West End

The West End is home to Moloka‘i’s has some condos, including a relic of Kaluakoi Resort; its 18-hole golf course closed long ago. The resort and the nearby reinvented plantation town of Maunaloa are secluded in a relatively unpopulated region, almost a half hour’s drive from other points of interest. It’s mostly home to high grassy bluffs, and many dirt roads that are off-limits to visitors.

Beaches along the shore are big and beautiful (especially the powder white sand Papohaku), though they’re usually unsafe for swimming. It’s not uncommon to have the beach all to yourself here. The West End might seem inhospitable, but it’s strangely alluring.

East End

The jungly East End—full of yawning valleys and lava cliffs—is subject to brief but intense rainstorms from December to March. Heading east on this 20-mile route, the twisting and turning landscape morphs from sandy shores to rocky coastline. Along the way you’ll pass fishponds, ancient heiau (temples), churches and a few condos and vacation rentals.

Venture to the East End on a weekday unless you want to experience Moloka‘i-style traffic: Parts of the too-narrow road are used as a sidewalk for pedestrians; parked cars pull off onto nonexistent shoulders, making for fun and challenging driving. When they say, “Slow down, you’re on Moloka‘i,” they aren’t kidding.

Thanks to Kim Grant for getting us started with this introduction.

Until we have a bit more time to round out our coverage, our Maui specialist has some specific ideas for you:

Big Wind Kites
Coffees of Hawaii
Halawa Park
Molokai Drive
Molokai Plumerias
Papohaku Beach Park
Purdy’s Mac Nut Farm

Get Started with this Molokai Itinerary

Moloka’€˜i Off the Beaten Path … Trip ideas for first-timers and repeat visitors


Leading a Mule Train, a personal account of the most popular activity on Moloka‘i

It’s pouring rain and it’s chilly and it’s really muddy, but we’re going. And we’re sizing each other up—we humans and those mules. Actually, the mules couldn’t care less whether it’s raining or how macho we are. Some riders are prepared with ponchos; others use makeshift garbage bags; one goes without, eager for the chance.

Mules, we quickly come to learn, have distinct personalities. And the owners of Moloka‘i Mule are quick to assess our personalities and play matchmaker with their beasts. None of us wants to be told what they’re seeing: Is our stubbornness or passiveness or fear written so clearly on our faces and in our body language?

I’m the last to settle into the saddle of my steed, and I quickly realize that I’ve been assigned the lead mule. How do I know? Because he knows. With great composure but intense determination, he quietly bulldozes his way past his compatriots to the front of the corral. Great . . . I’ve never led a mule train before; I’ve never even ridden a four-legged creature before. But it’s an honor to trust one’s life to the most trustworthy beast in the barn. After I give in to the trepidation—after all, these mules walk up and down this path day in and day out—the corral is opened, and off we trundle.

Down, down, down the 1,600-foot drop we go, toward the historic leper colony of Kalaupapa. At times the 3-mile trek seems nearly vertical. But that’s just because I’m perched 5 feet higher off the ground than usual and because my best friend, my mule, cuts corners. (I’ll never cut corners again; I promise.) He comes precariously close to each of the 26 switchbacks on the trail. He pauses at each turn, as if to carefully consider the best footing—shall we wedge the front hoof between rock and root or shall we let it slide ever-so-slightly before it lodges on that limb down there? He decides with what appears to be experienced haste. The trail is often no wider than his hoof. We pass a couple of hikers who are slip-sliding their way down. They actually look envious.

If there are two kinds of people in this world—passengers and drivers, as Volkswagen would have us believe—I’m normally a driver. And yet I’m quick to surrender the reins on this wet and woolly day. It takes a little while for me to become a passenger (until the third switchback or so), but it’s clear that my mule operates just fine without my intervention. Gradually my mule and I become one. We zig and zag together. My calves dangle alongside his rounded belly. Keeping my waist and hips loose, I let my shoulders sway back and forth with each sure step he places. I stop pretending (for whom?—the riders behind me so they’ll gain confidence?) to hold the reins loosely and let them rest on the pommel.

My mind’s mantra becomes let go and settle into it, a perfect metaphor for almost anything. I stop looking down and start looking around—drinking in the glorious scenery that perhaps didn’t feel so glorious to the residents who were struck with leprosy and “resettled” here. About the time I finish replaying their distressing story in my mind, we’ve reached the bottom of the trail, the rain has lifted, and it’s time to dismount and depart for the tour. My mule heads straight for a bale of hay at the end of the rainbow. He’s earned it—along with my respect. I look forward to ascending with him.

–Thanks to Kim Grant for this backstory.


Earlier last century, it was called the Lonely Isle, a place of  banishment for leprosy victims, a land of howling winds and scant population.

Going back into the mists of early Polynesian  civilization, Moloka‘i was revered and feared for the spiritual  strengths of its kahunas (priests). Lanikaula, a great prophet, lived  here as a hermit. Hula was born here. In the 17th century, the poisonwood gods created an aura of sorcery on the island. Father Damien, the heroic Belgian priest who tended the exiled lepers at Kalaupapa,  had a different faith but a similar intensity of devotion. The old  epithet Moloka‘i pule oo still caries meaning: The island remains “a  place of powerful prayers,” where ancient legends survive and abandoned  shrines and temples refuse to crumble completely.

Historically, Captain Cook never set foot here, but Protestant missionaries arrived in 1832. The landscape changed in 1848 when King Kamehameha V decreed that individuals could own land. By the 1870s, he had purchased much of the island from Rudolph Meyer (of the sugar mill fame). About 30 years after the king’s death in 1873, haole Charles Cook acquired the land and converted it into a cattle ranch, which, over the intervening years, produced pineapples, sugar, and honey. Today it survives as the defunct Molokai Ranch, which accounts for half of the land that is privately owned (or about a third of the entire island.)

–Thanks to Kim Grant for this backstory.


Father Damien & Moloka‘i’s Leper Colony

When Captain Cook arrived in Hawai‘i in 1778, the population of healthy Hawaiians was estimated at 250,000 to 300,000. By 1896—because of extremely infectious diseases like the plague, smallpox, cholera, influenza, and whooping cough introduced by foreigners—the population had plummeted to about 31,000. Leprosy, introduced as Ma‘i Pake (the Chinese sickness) in the early 1800s, was among the diseases.

Leprosy became an “official” concern of the Hawaiian Kingdom in 1865, when King Kamehameha authorized his government to acquire land specifically for the purpose of isolating its victims. Because it was such a highly visible and disturbing disease, victims were treated like criminals. If you were infected, it became illegal not to turn yourself in.

On January 6, 1866, the first “shipment” of leprosy sufferers was sent to Makanalua Peninsula on Moloka‘i’s north shore. Sent is perhaps too gentle a word, though. Because the land is surrounded on three sides by rough seas and the ship could not dock, patients were literally thrown overboard with a few of their belongings and left to swim ashore, holding on to what few belongings they could. Many did not make it. Because the peninsula is surrounded on the fourth side by steep 2,000-foot cliffs, the government assessed it an appropriate place to detain the victims and confine the disease. There was no way to escape.

By October 1866, 101 men and 41 women were stranded on the peninsula, boiling hot by day, fending for themselves without shelter or food. (Small amounts of food were sent from Honolulu; eventually, in 1887, the current-day mule and hiking trail was carved out of the mountainside to supply the community.) The community degenerated into lawlessness. Stories of the settlement trickled back to Honolulu, describing a desolate community filled with drunkenness and debauchery, where the strong took advantage of the weak.

These tragic accounts caused family members to hide loved ones afflicted with the contagious disease, which in turn caused it to spread more. Some healthy family members, not wanting their beloved to live and die on the peninsula alone, chose to accompany them—knowing that they themselves would never return.

In 1873, four Catholic priests (led by Bishop Louis D. Maigret) decided that the settlement desperately needed a full-time pastor to oversee things and minister to the sick and dying. They set up three-month rotations; Father Damien de Veuster went first and arrived on May 10. Two days after his arrival, the Belgian priest wrote the bishop: “I am willing to dedicate my life to the leprosy victims.”

Even though he made a quick and certain commitment to the people in the Kalaupapa community, Father Damien did not adjust to conditions quickly or easily. The sight of hundreds of people, many with extremely advanced cases of leprosy, was frightening. Since the smell and living conditions proved challenging, Father Damien began building sleeping quarters and started smoking a pipe to counteract the stench of open and draining sores. He did not sleep indoors until all the patients had housing.

Father Damien served as a nurse and doctor to the ailing, a parent to orphans, and a confidant and spiritual leader to the community. In a letter dated 1873, it’s said that Father Damien preached “We lepers” rather than “We brethren,” identifying himself with his flock long before he contracted the disease. More than 11,000 lepers arrived at the colony between 1866 and 1874.

Charles Warren Stoddard, who visited the settlement in 1868 and 1884, described Father Damien in The Lepers of Moloka‘i: “His cassock was worn and faded; his hair tumbled like a schoolboy’s, his hands stained and hardened by toil; but the flow of health was in his face, the buoyancy of youth in his manner; while his ringing laugh, his ready sympathy, and his inspiring magnetism told of one who in any sphere might do a noble work, and who in that which he has chosen is doing the noblest of all works.”

Father Damien was diagnosed with leprosy three months later. In all, he worked tirelessly with these patients for 11 years, until his death in 1889 at the age of 49.

Leprosy (more sensitively called Hansen’s disease) is now known to be caused by a bacillus, Mycobacterium leprae, and is one of the least communicable of all infectious diseases. In fact, only 5 percent of the world’s population is even susceptible to it. Even though drugs became available in the 1940s to cure the disease, many people infected by the disease chose to remain on the peninsula because it was the only home they’d known.

In December 1980, President Carter established Kalaupapa National Historical Park, ensuring that the site will be preserved for the future education of visitors and that remaining patients will be guaranteed privacy and the right to live there as long as they wish.

–Thanks to Kim Grant for this backstory.


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