Thirty-hour Getaway to Lānaʻi

How to pack a leisurely, luxurious vacation into less than a weekend? The answer is an island-hop away.


Story by Teya Penniman

visiting Lanai Hawaii from Maui
A short stroll from the resort lies Hulupo‘e Bay, whose protected waters teem with abundant marine life, including a local pod of spinner dolphins.

12:45 p.m. The sharp ridges and valleys of West Maui recede and soften as the Expeditions ferry crosses the ʻAuʻau Channel to Lānaʻi. The day is gloriously clear—each of Maui Nui’s islands joins the panorama, with Hawaiʻi Island emerging from a lei of clouds to the southeast. Our destination, Mānele Bay, is tucked around the south side of Lānaʻi, appearing like a surprise along the shoreline. As we approach the small-boat harbor, three dolphins pass beneath the ferry and a sea turtle surfaces. It’s a perfect welcome for the staycation my husband, Jay, and I will spend on Lānaʻi.

Lanai Hawaii Maui Getaway adventure
Inhale, relax, and unwind on pristine Lāna‘i at Four Seasons’ Five Diamond resort, whose sumptuous suites face the secluded island’s sprawling southeastern coast. Guests can enjoy a guided stroll through lush botanical gardens or stop to “talk story” with Uncle Bruno, the resort’s aviarist, and his feathered rescue bird friends.

2 p.m. Arriving at the Four Seasons, we’re impressed by the resort’s transformation since our last visit. The previous mélange of Mediterranean and Asian architectural styles has morphed into an aesthetic that truly conveys a sense of place. The walls and floors capture the umber sand and red-earth tones of the island. Whale-vertebrae sculptures and wall insets of giant shells remind that the ocean is just steps away. The gardens abound in tropical flora. I’d be happy lounging on the lānai for a few hours, gazing out to sea, but our scheduled carriage ride leaves just enough time for some pūpū (appetizers) and beverages at the Four Seasons’ Malibu Farm restaurant before heading up to the Stables at Kōʻele.

Lanai Hawaii horse carriage
Opt for a leisurely way to see Lāna‘i and clip-clop around the charming town on a horse-drawn carriage ride arranged by the Stables at Kō‘ele.

4 p.m. “We cause the only traffic jam on Lānaʻi,” jokes Mary Klein, the woman at the reins, as a pickup truck waits to pass our horse-drawn carriage clip-clopping its way around Dole Park, the center of Lāna‘i City. “We sometimes have a two- to three-car buildup.” Our slow-and-steady power source is Ben, an English Shire draught horse brought to Lānaʻi with brother Pete to launch the leisurely excursion. Some 3,100 people reside in this “city” that spans fourteen streets wide and long. There are no traffic lights here—or anywhere on the island. And everyone waves.

Our driver is the real deal. Born and raised on Maui, Mary started competing in all things equestrian by the age of nine. Her father, a farrier, taught her how to shoe a horse, but these days, the stables are taking a different tack. “We are completely shoe-free,” Klein says, explaining that going bare-hoofed allows the animals’ feet to expand and contract naturally.

She points out highlights and history as we wind our way through town: the local bank featured on statewide commercials, the gas station, the public gym, a handful of eateries, and the local college. “What’s for dinner?” she calls to the family with a front-yard barbeque in progress. The griller, a chef at Malibu Farm, is evidently enjoying a busman’s holiday.

More than 90 percent of the island is owned by Pūlama Lāna‘i (owned in turn by tech giant Larry Ellison). The company has been restoring some of the town’s venerable buildings, including the old courthouse and a woodshop where workers previously sorted pineapples. There are no Starbucks, but you can purchase your cappuccino-latte-whatever at Coffee Works daily—except Sundays. The carriage ride is a relatively new addition to the suite of activities for Lānaʻi visitors. “It’s the best way to feel like a celebrity,” Mary says, as keiki come running to check it out.

Lanai Hawaii adventure
ENCHANTED EVENINGS begin with a table along Hulopo‘e Bay to savor a few chef specialties and toast a day well spent.

6:30 p.m. We arrive at the Four Seasons’ open-air One Forty restaurant, named for the number of square miles that make up the island, in time to catch the fading view of Hulopoʻe Bay and the moon arcing up into an inky sky. Celebratory flutes of champagne, the chef’s selection of sweet oysters, and a salad of Waipoli butter lettuce start the repast. We share a delicate, locally caught ʻōpakapaka (snapper), and a buttery wagyu New York strip steak topped with braised chestnuts, caramelized onions and roasted mushrooms. Wisely following our carriage driver’s advice, we add a side of lobster mashed potatoes. But I’m fairly sure it’s the bottle of “One Forty” that causes us to be among the guests closing the restaurant. Crafted exclusively to pair with the venue’s signature beef dishes, the Napa Valley cabernet sauvignon is exquisite, the last drops melding nicely with the outside-crunchy, inside-molten chocolate soufflé that tops off our meal.

Lanai Hawaii Maui Getaway
Fishing in waters off Lāna‘i might reel in more than a mahimahi or yellow-fin tuna: whale sharks, manta rays, and humpbacks are all known to make surprise visits during ocean adventures.

9:30 a.m. We learned last night that this morning’s near-dawn, deep-sea fishing excursion has been rescheduled—to noon. So after a quick breakfast, we take the gently sloping path down to Hulopoʻe Beach, one of my favorites. Both Hulopoʻe and Mānele Bay are marine preserves, where only shoreline fishing is allowed. Clear and calm waters prevail, and an easy snorkel over coral reefs reveals spectacled parrotfish, convict and yellow tangs, and goatfish. They, too, seem to be in relax mode, allowing the gentle, oscillating surge to carry them back and forth, midwater or at the bottom of sandy channels.

12 p.m. At the harbor, Captain Ricky Etrata and deckhand Chris Stoehr (also a licensed captain) welcome us aboard the Kalulu, a thirty-nine-foot, rigid-bottom inflatable with a past life as a chase boat for the America’s Cup. Its three 250-horsepower engines could reach Lahaina in a mere twenty minutes, but we’re headed in the opposite direction, to waters off Lānaʻi’s southwest flank. Captain Ricky shares details about the small fleet of boats that make up Lānaʻi Ocean Sports. We’re in good hands: for the last twenty years he’s captained snorkel tours, dive-certification trips, and sunset sails, from small, private rentals to the Lānaʻi V, which can hold up to thirty passengers.

Winds often kick up in the afternoon around the islands, but our luck holds and the sea chop is mild. After trolling unsuccessfully in deeper waters, Captain Ricky bring us closer to shore, where sheer coastal bluffs rise more than 1,000 feet, the highest south-facing cliffs in Hawai‘i. “Fish on!” hollers Chris, pointing to the taut line off the stern. The reeling-in is effortless and it feels like a bit of puffery to claim I landed this gorgeous creature with sapphire-blue fins and a splattering of blue spots on moss-green sides. Pāpio are young ulua, also known as jacks or trevally. Ricky estimates its size at eight pounds. Jay’s seemingly simple question, “What’s your favorite fish to catch?” inspires a lengthy and appreciative discourse by Ricky on the different species fished around Lānaʻi.

We land another two and lose one before turning back. As we close out the last of our adventures, it’s hard to believe that several hours have passed on the water with barely another soul in sight.

4:30 p.m. On the return trip to Maui, I’m struck not just by the slow pace Lāna‘i induces, nor the delicious sense of seclusion, but also the feeling of being embraced by the island, and the kindness and genuine openness of the people we met. As with all good journeys, my only regret is that it’s over much too soon, with so much left unexplored. The pāpio accompanying us home promises to be a wonderful consolation.

Lanai Hawaii visit

Relax. There’s More.

Despite Lānaʻi’s laid-back vibe, you could easily fill a week with activities and culinary experiences at the Four Seasons and in town. Outdoor activities available through the resort include guided horseback rides, sporting clays, off-road touring, golf and tennis, and a suite of boat-based trips. More sedate options include cultural activities, poolside or beach lounging, mixology (and tasting) classes, and the spa and fitness center. Or poke around Lānaʻi City on your own, exploring local galleries, shops, and the Lāna‘i Culture and Heritage Center.

Four Seasons Resort Lānaʻi: 808-565-2000;


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