For many, Maui inhabits the sweet spot. It’s a tangle of lovely contradictions, with a Gucci heel on one foot and a puka-shell anklet on the other. Culturally, it’s a mix of farmers, paniolo (Hawaiian cowboys), aspiring chefs, artists, New Age healers, and big wave riders. The landscape runs the gamut from sun-kissed golden beaches and fragrant rainforests to the frigid, wind-swept summit of Haleakala. Sure, more traffic lights sprout up around the island every year and spurts of development have turned cherished landmarks into mere memories. But even as Maui transforms, its allure remains.

The Island in Brief

This medium-sized island lies in the center of the Hawaiian archipelago.

Central Maui

Maui, the Valley Isle, is so named for the large isthmus between the island’s two towering volcanoes: Haleakala and the West Maui Mountains. The flat landscape in between, Central Maui, is the heart of the island’s business community and local government.

Kahului--Most Maui visitors fly over waving sugarcane fields to land at Kahului Airport, just yards away from rolling surf. Sadly, your first sight out of the airport will likely be a Costco—hardly an icon of Hawaiiana but always bustling with islanders and visitors alike. Beyond that, Kahului is a grid of shops and no-nonsense neighborhoods that you’ll pass through en route to your destination.

Wailuku--Nestled up against the West Maui Mountains, Wailuku is a time capsule of faded wooden storefronts, old churches, and plantation homes. While most people zip through on their way to see the natural beauty of Iao Valley, this quaint little town is worth a brief visit, if only to see a real place where real people actually appear to be working at something other than a suntan. This is the county seat, so you’ll see folks in suits (or at least aloha shirts and long pants) on important missions in the tropical heat. The town has some great budget restaurants, interesting bungalow architecture, a wonderful historic B&B, and the intriguing Bailey House Museum.

West Maui

Jagged peaks, velvety green valleys, a wilderness full of native species: The majestic West Maui Mountains are the epitome of earthly paradise. The beaches below are crowded with condos and resorts, but still achingly beautiful. This stretch of coastline along Maui’s “forehead,” from Kapalua to the historic port of Lahaina, is the island’s busiest resort area (with South Maui close behind). Expect slow-moving traffic on the two main thoroughfares: Honoapiilani Highway and Front Street.

Vacationers on this coast can choose from several beachside neighborhoods, each with its own identity and microclimate. The West Side tends to be hot, humid, and sunny year-round. As you travel north, the weather grows cooler and mistier. Starting at the southern end of West Maui and moving northward, the coastal communities look like this:

Lahaina--In days past, Lahaina was the seat of Hawaiian royalty. Legend has it that a powerful mo‘o (lizard goddess) dwelt in a moat surrounding a palace here. Later, this hot and sunny seaport was where raucous whalers swaggered ashore in search of women and grog. Modern Lahaina is a tame version of its former self. Today Front Street teems with restaurants, T-shirt shops, and galleries. Action revolves around the town’s giant, century-old banyan tree and busy recreational harbor. Parts of Lahaina are downright tacky, but you can still find plenty of authentic history here. It’s also a great place to stay; accommodations include a few old hotels (such as the 1901 Pioneer Inn on the harbor), quaint bed-and-breakfasts, and a handful of oceanfront condos.

Kaanapali--Farther north along the West Maui coast is Hawaii’s first master-planned destination resort. Along nearly 3 miles of sun-kissed golden beach, pricey midrise hotels are linked by a landscaped parkway and a beachfront walking path. Golf greens wrap around the slope between beachfront and hillside properties.Convenience is a factor here: Whalers Village shopping mall and numerous restaurants are easy to reach on foot or by resort shuttle. Shuttles serves the small West Maui airport just to the north and also go to Lahainaah, for shopping, dining, entertainment, and boat tours. Kaanapali is popular with groups and families—and especially teenagers, who like all the action.

Honokowai, Kahana--In the building binge of the 1970s, condominiums sprouted along this gorgeous coastline like mushrooms after a rain. Today, these older oceanside units offer excellent bargains for astute travelers. The great location—along sandy beaches, within minutes of both the Kapalua and Kaanapali resort areas, and close enough to the goings-on in Lahaina town—makes this area a haven for the budget-minded.

In Honokowai and Mahinahina, you’ll find mostly older, cheaper units. There’s not much shopping here (mostly convenience stores), but you’ll have easy access to the shops and restaurants of Kaanapali. Kahana is a little more upscale than Honokowai and Mahinahina, and most of its condos are big high-rise types, newer than those immediately to the south.

Napili--A quiet, tucked-away gem, with temperatures at least 5 degrees cooler than in Lahaina, this tiny neighborhood feels like a world unto itself. Wrapped around deliciously calm Napili Bay, Napili offers convenient activity desks and decent eateries and is close to the gourmet restaurants of Kapalua. Lodging is generally more expensive here—although I’ve found a few hidden jewels at affordable prices.

Kapalua--Beyond the activity of Kaanapali and Kahana, the road starts to climb and the vista opens up to include unfettered views of Molokai across the channel. A country lane lined with Cook pines brings you to Kapalua. It’s the exclusive domain of the luxurious Ritz-Carlton resort and expensive condos and villas, set above two sandy beaches. Just north are two jeweled bays: marine-life preserves and world-class surf spot in winter. Although rain is frequent here, it doesn’t dampen the enjoyment of this wilder stretch of coast.

Anyone is welcome to visit Kapalua, guest of the resort or not. The Ritz-Carlton provides free public parking and beach access. The resort has swank restaurants, spas, golf courses, and hiking trails—all open to the general public.

South Maui

The hot, sunny South Maui coastline is popular with families and sun worshippers. Rain rarely falls here, and temperatures hover around 85[dg]F (29[dg]C) year-round. Cows once grazed and cacti grew wild on this former scrubland from Maalaea to Makena, now home to four distinct areas—Maalaea, Kihei, Wailea, and Makena. Maalaea is off on its own, at the mouth of an active small boat harbor, Kihei is the working-class, feeder community for well-heeled Wailea, and Makena is a luxurious wilderness at the road’s end.

Maalaea--If West Maui is the island’s head, Maalaea is just under the chin. This windy, oceanfront village centers on a small-boat harbor (with a general store and a handful of restaurants) and the Maui Ocean Center, an aquarium/ocean complex. Visitors should be aware that tradewinds are near constant here, so a stroll on the beach often comes with a free sandblasting.

Kihei--Kihei is less a proper town than a nearly continuous series of condos and mini-malls lining South Kihei Road. This is Maui’s best vacation bargain. Budget travelers swarm like sun-seeking geckos over the eight sandy beaches along this scalloped, 7-mile stretch of coast. Kihei is neither charming nor quaint; what it lacks in aesthetics, though, it more than makes up for in sunshine, affordability, and convenience. If you want the beach in the morning, shopping in the afternoon, and Hawaii Regional Cuisine in the evening—all at bargain prices—head to Kihei.

Wailea--Just 4 decades ago, the road south of Kihei was a barely paved path through a tangle of kiawe trees. Now Wailea is a manicured oasis of multimillion-dollar resorts along 2 miles of palm-fringed gold coast. Wailea has warm, clear water full of tropical fish; year-round sunshine and clear blue skies; and hedonistic pleasure palaces on 1,500 acres of black-lava shore indented by five beautiful beaches, each one prettier than the next.

This is the playground of the stretch-limo set. The planned resort development has a shopping village, a plethora of award-winning restaurants, several prized golf courses, and a tennis complex. A growing number of large homes sprawl over the upper hillside, some offering excellent B&Bs at reasonable prices. The resorts along this fantasy coast are spectacular. Next door to the Four Seasons Resort Maui at Wailea, the most elegant, is the Grand Wailea, built by Tokyo developer Takeshi Sekiguchi, who dropped $500 million in 1991 to create the most opulent Hawaiian resort to date. Stop in and take a look—sculptures by Botero and Leger populate its open-air art gallery and gardens. Stones imported from Mount Fuji line the Japanese garden fronting the resort’s Amasia restaurant.

Makena--Suddenly, the road enters raw wilderness. After Wailea’s overdone density, the thorny landscape is a welcome relief. Although beautiful, this is an end-of-the-road kind of place: It’s a long drive from Makena to anywhere on Maui. If you’re looking for an activity-filled vacation, stay elsewhere, or you’ll spend most of your vacation in the car. But if you want a quiet, relaxing respite, where the biggest trip of the day is from your bed to the beach, Makena is the place.

Puu Olai stands like Maui’s Diamond Head near the southern tip of the island. The red cinder cone shelters tropical fish and Makena State Beach Park, a vast stretch of golden sand spanked by feisty swells. Beyond Makena, you’ll discover Haleakala’s most recent lava flow; the bay named for French explorer La Pérouse; and a sunbaked lava-rock trail known as the King’s Highway, which threads around Maui’s southernmost shore through the ruins of bygone fishing villages.

Upcountry Maui

After a few days at the beach, you’ll probably notice the 10,023-foot mountain towering over Maui. The leeward slopes of Haleakala (House of the Sun) are home to cowboys, farmers, and other rural folks who wave as you drive by. They’re all up here enjoying the crisp air, emerald pastures, eucalyptus, and flower farms of this tropical Olympus. The neighborhoods here are called “upcountry” because they’re halfway up the mountain. You can see a thousand tropical sunsets reflected in the windows of houses old and new, strung along a road that runs like a loose hound from Makawao to Kula, leading up to the summit and Haleakala National Park. If you head south on Kula Highway, beyond the tiny outpost of Keokea, the road turns feral, undulating out towards Tedeschi Winery, where grapes, cattle, and elk flourish on Ulupalakua Ranch. A stay upcountry is usually affordable and a nice contrast to the sizzling beaches and busy resorts below.


Makawao--This small, two-street town has plenty of charm. It wasn’t long ago that Hawaiian paniolo (cowboys) tied up their horses to the hitching posts outside the storefronts here; working ranchers still stroll through to pick up coffee and packages from the post office. The eclectic shops, galleries, and restaurants have a little something for everyone—from blocked Stetsons to wind chimes. Nearby, the Hui No‘eau Visual Arts Center, Hawaii’s premier arts collective, is definitely worth a detour. Makawao’s only accommodations are reasonably priced bed-and-breakfasts, perfect for those who love great views and don’t mind slightly chilly nights.

Kula--A feeling of pastoral remoteness prevails in this upcountry community of old flower farms, humble cottages, and new suburban ranch houses with million-dollar views that take in the ocean, the isthmus, the West Maui Mountains, and, at night, the lights that run along the gold coast like a string of pearls from Maalaea to Puu Olai. Everything flourishes at a cool 3,000 feet (bring a jacket), just below the cloud line, along a winding road on the way up to Haleakala National Park. Everyone here grows something—Maui onions, lavender, orchids, and proteas—and B&Bs cater to guests seeking cool tropical nights, panoramic views, and a rural upland escape. Here you’ll find the true peace and quiet that only rural farming country can offer—yet you’re still just 30 to 40 minutes away from the beach and an hour’s drive from Lahaina.

On the Road to Hana--On Maui’s north shore, Paia was once a busy sugar plantation town, with a railroad, two movie theaters, and a double-decker mercantile. As the sugar industry began to wane, the tuned-in, dropped-out hippies of the 1970s moved in, followed shortly by a cosmopolitan collection of windsurfers. When the international wave riders discovered Hookipa Beach Park just outside of town, their minds were blown; it’s one of the best places on the planet to catch air. Today, high-tech windsurf shops, trendy restaurants, bikini boutiques, and modern art galleries inhabit Paia’s rainbow-colored vintage buildings. The Dalai Lama himself blessed the beautiful Tibetan stupa in the center of town. Mama’s Fish House is located east of Paia, in the tiny community of Kuau.

Ten minutes farther east is Haiku. Once a pineapple plantation village, complete with two canneries (both now shopping complexes), Haiku offers vacation rentals and B&Bs in a pastoral setting. It’s the perfect base for those who want to get off the beaten path and experience the quieter side of Maui.

Hana--Set between an emerald rainforest and the blue Pacific is a Hawaiian village blissfully lacking in golf courses, shopping malls, and fast-food joints. Hana is more of a sensory overload than a destination; here you’ll discover the simple joys of rain-misted flowers, the sweet taste of backyard bananas and papayas, and the easy calm and unabashed aloha spirit of old Hawaii. What saved “Heavenly” Hana from the inevitable march of progress? The 52-mile Hana Highway, which winds around 600 curves and crosses more than 50 one-lane bridges on its way from Kahului. You can go to Hana for the day—it’s 3 hours (and a half-century) from Kihei and Lahaina—but 3 days are better.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.