Lānaʻi, Then and Now

Learn the ancient history of Lāna‘i, and discover how to best experience it today.

Text by Ellie Crowe and Lisa Yamada-Son
Images by John Hook

The 140-square-mile island of Lāna‘i has gone through numerous iterations since its volcanic birth roughly one million years ago. It has been home to malevolent spirits and sorcerers, which were expelled by a Hawaiian prince. It became, briefly, the pineapple-growing capital of the world. Today, this island, which is now owned by Oracle founder Larry Ellison, offers a balance of quiet beach time and adventurous excursions.

Though Lāna‘i is now known as a place of refuge and relaxation, this idyllic island was once uninhabitable, according to legend. Until the 15th century, the island was kapu, or forbidden, to visit because it was home to dangerous spirits. Fortunately, they are gone now, having been exorcised by Kaululā‘au, a 12-year-old boy.

The son of the king of Maui, Kaululā‘au was a rascal. In fact, it was Kaululā‘au who led boys on the island to paint the prized pigs, imitated the death-bird’s hoot in the village at night, and pushed fishing canoes out to sea. Then, one dark night, Kaululā‘au went too far and uprooted a grove of young breadfruit trees planted by the king. Destroying even one of these precious trees was punishable by death, but instead of being executed, Kaululā‘au was banished to Lāna‘i—a fate considered to be a certain death sentence.

War canoes took the young boy across the windswept channel to the dark island, and landed at Kahalepalaoa, where the spirits attempted to kill the exiled prince. Ever cunning, Kaululā‘au built a hut at the top of peaked Lāna‘ihale, invited them over, and served intoxicating ‘awa. When the spirits fell asleep, he gummed their eyelids with bird lime and set fire to the hut.

After defeating the former residents, Kaululā‘au lit a huge bonfire at Naha on the eastern coast, the closest point to Maui. At the sight of the glowing flames, the king guessed of his son’s courageous acts. The king sailed to Lāna‘i and nominated his brave son the ruling chief of the island. Translating to “day of conquest,” the island’s name, Lāna‘i, harkens back to the clever Kaululā‘au, who tricked the spirits and sorcerer of this small isle.

Today, travelers to Lāna‘i can visit the same sites that Kaululā‘au encountered. Kahalepalaoa, the beach where he first landed, has historical sites to explore and great snorkeling, and is reachable by 4×4 Jeep. Heading inland, the Munro Trail at the center of the island ascends 12 scenic miles to the 3,370-foot high peak of Lāna‘ihale (House of Lāna‘i).

Of course, much has changed on Lāna‘i since Kaululā‘au became its ruling chief. Horses and their natural counterparts, paniolo, or cowboys, have taken up residence, as have mouflon sheep and axis deer. This gives the island a pastoral feel, which is matched by country adventures, such as horseback riding and hunting excursions. The island now has a town, aptly named Lāna‘i City, though not enough residents to warrant even a single stoplight.

For those who want to embrace this small-town charm for their visit, Hotel Lāna‘i offers a welcoming nod to the past, complete with wood-framed walls and whitewashed plank ceilings, hand-sewn quilts, and occasionally creaky floorboards in the classic Hawaiian plantation style. Located at the heart of Lāna‘i City, the hotel offers proximity to the only semblance of metropolitan life, as well as cooler mornings among Cook Pines. Within walking distance is the Lāna‘i Culture and Heritage Center, where the history of the island is laid out on the walls and embodied within the cultural artifacts on display.

If it’s sunny skies and luxurious relaxation that you are looking for, make Four Seasons Resort Lāna‘i, perched above Hulopo‘e Bay, your home base. Under Ellison’s ownership, this resort received a major makeover, including a new pool, upgraded interiors, sprawling suites, and high-tech accoutrements befitting an island hotel that is owned by a tech magnate. While it is some distance from the main town, this secluded nature is part of its allure—the resort truly feels like an escape from reality.

Built atop the low-slung cliffs of Hulopo‘e Bay, Four Seasons overlooks a white sand beach fronting the crystal clear water of a marine sanctuary. Walk over for some snorkeling, or take a quick 15-minute hike further to Pu‘u Pehe, also known as Sweetheart Rock, where dramatic cliffs accent the aquamarine tide pools below. After a hot day spent in the sun, lounge by the resort’s sparkling blue pool with a refreshing cocktail from the pool bar and tapas from onsite restaurant, Nobu Lāna‘i

Four Seasons Resort Lāna‘i also offers ways to experience the island’s wilder side, like an archery range, a shooting range, and off-road excursions. Or, rent a Jeep and travel the lengths of the island on your own. About 45 minutes from the resort, on the island’s northeast coast, is Shipwreck Beach, which was named for an abandoned barge that rests on the reef offshore.

If you would rather head inland, Keahiakawelo, commonly called Garden of the Gods, lies six miles west of Lāna‘i City. This rocky desertscape at the end of Polihua Road makes apparent, once again, just how timeless the island of Lāna‘i truly is.