Escape to Wailea, Hawaii

Craig OuthierMay 3, 2019
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Nightly torch lighting at the Fairmont Kea Lani; Photo courtesy Fairmont Kea Lani
Nightly torch lighting at the Fairmont Kea Lani; Photo courtesy Fairmont Kea Lani

Have a Maui wowie of a vacation on the island’s beatific leeward coast.

“Huh. rain.”

That’s my expert meteorological assessment as I clobber a plate of fish tacos and eye a rolling bank of storm clouds that has suddenly gathered over Maui’s Haleakala volcano, seemingly just a few miles inland from where we’re sitting in the coastal resort town of Wailea.

“Oh, maybe not,” my dining companion, a local, politely demurs after quickly registering the low, horizontal formation, which my nerdy high school speech-team buddy would have called an “arcus” cloud. “You see those every day on this part of the island. You think they’re coming for us but they never do. They just sit there.”

A couple hours later, enjoying the pool at a resort, I see she’s correct: The ominous clouds haven’t budged. They are just sitting there, like a shuffling clique of junior high boys too bashful to ask for a dance. It’s sunny and perfect.

That, among other things, is the magic of Wailea, set on the southern half of Maui’s leeward (read: non-wind-facing) west coast. While the island’s rugged eastern half is doused with 300 inches of average rainfall a year, Wailea and other leeward towns get about 15 inches. It’s one of those wonky, heady factoids that pairs so nicely with the raw, soul-striking beauty of Hawaii, with its dizzying variety of microclimates and bipolar weather displays.

Located on an island some have likened to a hybrid of urbanized Oahu and unspoiled Kauai, Wailea is well-positioned to sample Maui’s other magical traits, too. Because there’s more to a Hawaiian vacation than not getting wet.

When to Visit

When not to visit, more like. The island can get a bit hazy in fall and winter when the “Kona winds” arrive from the southwest.


Reminiscent of La Jolla, Rancho Palos Verdes and other well-planned, high-dollar coastal settlements, Wailea is essentially a 3-mile phalanx of ridiculously gorgeous beachfront resorts – five in all, each with its own, subtly different approach to whisking you off to luau fantasy land. At the north end is the Andaz Maui at Wailea Resort, a petite, modern property in the hip Andaz mold (3550 Wailea Alanui Dr., 808-573-1234,, $600/night in the summer). Moving south, you’ll find the elegant, Orient-inspired sparseness of Wailea Beach Resort, its grounds covered in Maui’s giant bonsai monkeypod trees (3700 Wailea Alanui Dr., 808-879-1922,, $600).

Round a point and you’ll find the Grand Wailea – Maui’s largest and most impressive resort, with a yawning, temple-like breeze-through lobby and the choicest piece of beachfront of all the Wailea properties (3850 Wailea Alanui Dr., 808-875-1234,, $500/night). With its scores of families and newlyweds, and sprawling, winged layout, the Grand has a definite Epcot/Disneyworld gestalt to it – one that immerses you almost instantly in its beach-spaceship vibe. On the topic of immersion, its spa – ranked one of the Top 10 in the U.S. by both Condé Nast Traveler and Travel + Leisure – is a true showstopper, with “healing water” baths in five different aromatic styles, and a dazzling variety of exotic showers and vertical flows, including a scalp-thumping waterfall that slipped me into an instant pleasure coma.

Naturally, the Four Seasons Resort Maui at Wailea (3900 Wailea Alanui Dr., 808-874-8000,, $900/night) has staked out a piece of Wailea, just south of the Grand. Just as naturally, it evinces a wisp of neoclassical hauteur in its design – all columns and stern lines. Finally, at the southern end of Wailea’s resort row is the Fairmont Kea Lani, a sprawling canvas of footpaths, grassy meadows and swimming pools for every demographic (4100 Wailea Alanui Dr., 808-875-4100,, $575/night). With its dramatic sunset-viewing mezzanines and large, dedicated beach, the Fairmont struck me as the most versatile of the Wailea resorts – definitely scene-y enough for groups and gregarious couples, but with plenty of opps for solitude, too. It also had the best bar, LUANA, which holds Monday mixology classes and serves sensational tiki-inspired cocktails. My favorite: Any Port in a Storm, combining rum, rye and Antica with a grilled pineapple shrub and house-made bitters. Definitely not your typical hotel grog.

Biking down Haleakala; Photo by Craig Outhier
Biking down Haleakala; Photo by Craig Outhier


It’s 1:45 a.m. on my first night in Wailea when the iPhone alarm next to my bedside dutifully sounds. This unforgivable act of masochism is redeemed exactly four hours and 17 minutes later, as I watch the sun crown over the Pacific from my 10,000-foot vantage atop Haleakala. It’s an exalting, mind-expanding display of color and reanimation, and my main impetus for visiting Maui in the first place.

That, and the ride back. As part of its Haleakala “Sunrise Special,” local tour company Bike Maui ( picks you up at your hotel, deposits you on top of the mountain with several dozen other sunrise-seekers, then provides you with a sturdy mountain bike so you can peacefully glide down Haleakala, passing through an absolutely stunning kaleidoscope of ecosystems, weather systems and biomes on your way back to the bike shop. You also pass by Oprah Winfrey’s mountainside mansion, I’m told.

Saying you bike “off” the mountain isn’t really accurate – 75 percent of Maui is technically Haleakala, which last erupted in the 1700s and is woven into the popular consciousness here just as the Sonora is back home. Which is why the sunrise/bike experience gets my heartiest rec. It’s spirituality, fitness and ecology all rolled into one. The friendly guides shuck it up nicely, too, which helps take the edge off the tedium during the two-hour, pitch-black drive up the mountain.

Closer to my homebase in Wailea, I later embark on another Haleakala-esque adventure: the King’s Trail hike, offered by the Fairmont Kea Lani. Driving south out of Wailea into the undeveloped Ahihi-Kinau Natural Area Preserve, we meet up with the titular trail, a coast-hugging path that cuts through lava fields commissioned by a pre-colonial Hawaiian king that once encompassed the entire, 727-square-mile island. We see wild coyotes, frothy tide pools and 4-by-4-ing hippie fisherman, all under the gaze of Haleakala and slopes of jagged, 300-year-old rock.

Later, I cool off with a quick dip in the ocean at the Fairmont – which, like the Grand Mayan, has walk-in snorkeling right off the beach, with plenty of interesting fish to gawk at. My whistle for parrotfish whetted, I enlist in the Molokini & Turtle Town Dive with Maui Dive Shop (808-879-1775, – a three-hour scuba excursion to Maui’s uninhabited satellite island and nearby reef beds. These are relatively shallow reefs – 12 to 15 feet – so the dive company invites snorklers to join, too. It’s great for couples if one person is certified and the other isn’t.

lemongrass-coconut sea bass at Ko at the Fairmont Kea Lani; Photo courtesy Ko/Fairmont Kea Lani
lemongrass-coconut sea bass at Ko at the Fairmont Kea Lani; Photo courtesy Ko/Fairmont Kea Lani


Dining in Maui is a classic high-low proposition: chichi resort fare on one hand, scrappy food huts and poi lunch plates on the other… though you may have to break free of Wailea’s sybaritic grip to sample the latter.

For pure, wow-factor scenery, you won’t do better than Humuhumunukunukuapua’aHumuhumu for short – the flagship restaurant at the Grand Wailea, set in a spectacular Polynesian open-air lodge raised on stilts over a lagoon next to the ocean. The Humu Seafood Tower is just as eye-pleasing, tiered with oysters, seared ahi poke, king crab and more – a true welcome-to-Hawaii conversation piece.

In addition to the shockingly good small-plate pub fare at LUANA – including the most exciting Korean-style chicken wings I’ve ever tasted, served with a ramekin of kimchi hummus – the Fairmont sports one of Wailea’s best Asian restaurants, Ko. This is where you want to load up on ahi crudo (with kaiwarae sprouts and orange-wasabi drizzle) and other seafood delicacies, all informed by a farm-to-table sensibility. The specialty of the house is the fresh catch of the day wrapped in the broad, green leaf of the ti plant, used in traditional Polynesian medicine, which imparts a lovely vegetal, slightly bitter counterpoint to the mango salsa and Molokai sweet potato served with the fish.

After dining on fussy resort fare for a few days, I was ready for some soul food – specifically, a Hawaiian barbecue plate lunch. I found a superb one at Da Kitchen Express (2439 S. Kihei Rd., Kihei, 808-875-7782, up the coast a bit in nearby Kihei, which is sort of the budget bookend community to Wailea, with hotel rooms that go for about a quarter of the price. Da Kitchen serves huge portions of katsu pork, loco moco (egg topped with a ground beef patty and fried egg), teriyaki chicken and more, served with Hawaiian macaroni salad, simmered greens and rice, with all the hoisin and sriracha you can dumb on it. Glorious.

“You should really visit Mama’s Fish House if you want a classic Maui meal,” a local acquaintance tells me. “Like, gourmet-quality seafood dishes, but served in a little shack, on funky old ceramic plates. But it’s kind of far from your hotel, on the north side of the island.”

Luckily, the “other side of the island” means a mere 30-minute drive from Wailea to the windward side. That’s the upside of tearing yourself away from the Wailea amnion – it’s not too far from anything. Just prepare to get rained on.

Lahaina LowDown

Though it’s situated just a 40-minute drive up the leeward coast from Wailea, the tourist hot spot of Lahaina feels like a different island – it has its own airport, its own beach culture, even its own dormant volcano. Here are three suggestions for a day trip or longer stay:

Sheraton Maul Resort & Spa
Maui’s first resort is a fascinating study in geological hospitality – in the far extremities of the property, built into the cliffs above the main entry and guestroom buildings, you’ll find the original porte-cochère and classic, Mad Men-era lobby, now a special event space. This large, fun-filled resort is an activities bonanza, including the island’s best beachside snorkeling.

Slaughterhouse Beach
Dozens of beautiful beaches and parks dot the coastline north of Lahaina on the Honoapiilani Highway, but none is as cool as this secluded, sheltered inlet, accessible only by a stairwell that descends into a shaded weald from the highway.

Kahekili Highway
Take a wrong turn out of the car rental agency in Lahaina, and you’ll find yourself circumnavigating Maui via a some-times hairy one-lane road past plantations, art colonies and wild, untamed fauna encircling north Maui’s Pu‘u Kukui mountain. Call it a happy accident.