Maui On My Mind

Why the nation’s 50th state is its number one place to chill out and get right with the world.

  • Aerial view of Kahului
  • Windsurfing Maui’s north shore
  • traveling the Road to Hana
  • Four Seasons Hotels and Resorts
  • Maui waterfall
  • Caldera of the Haleakala
  • Pool at Grand Wailea Resort
  • Lahaina at dusk.
  • Travaasa Hana
  • Honu Seafood & Pizza

When I returned from MEA weekend with a suntan, folks asked where I’d been. When I told them Maui, several responded with incredulity. “Hawaii? For five days?” (We stole a sixth.) “Ever heard of Miami or Newport Beach?” one asked. Another noted he could be in the Bahamas four hours faster.

All legitimate points, to be sure. Hawaii is far (4,000 air miles far, the same as London, basically). Delta eliminated the nonstop flight last year. Hawaii is expensive ($13 mai tais anyone?). And for all that effort, you don’t even get a stamp on your passport. What’s the appeal, then? Ask anyone who’s been.

I’ve been going to Hawaii for two decades now, probably averaging a trip every two years, and can tell you it’s the one place in the world I never get bored with or fail to be rejuvenated by. It is, to me, the perfect relaxation vacation.

And Hawaii feels special enough to justify the distance. It’s not just another beach spot. The Islands offer every type of experience, from the gritty vertical urban vibe of Honolulu to the tourist-wary wilds of Molokai to the luxe resorts and private-island feel of Lana’i. I’ve come to love Maui for its combination of beautiful resorts, manageable size, richness of amenities, magnificent natural areas, and an interesting California meets South Pacific sensibility.

The other thing that sets Hawaii apart is its sheer beauty. Despite all the development, even in vertical Oahu, you’re never more than a 15-minute drive from a waterfall, ocean promontory, or mountain vista. The sky is deep blue, the night sky inky black, the volcanic soils almost red, and the verdant slopes a vivid green. Hawaii is a riot of texture, a kaleidoscope of color.

But what you’ll notice most is the friendliness. For a place beset by tourists, Hawaiians take it in stride. There’s none of the colonial-racial tension so palpable in the Caribbean, none of the blasé disdain you experience in Florida. Hawaiians are blessed, they know it, and they don’t seem to mind us dropping in on them. Aloha, indeed.

If you’ve never been, or haven’t been in a while, here are five seminal Maui experiences. Follow my agenda and you’ll leave a convert.

A Day at the Beach (Resort): Maui has so many great beachfront resorts that it’s hard to recommend one (though I’ll try later). But a huge part of the Hawaii experience is its glorious beaches, incredible resort pools, and laying back on a chaise with a drink and blissing out. It may bore your kids silly, but we all need this. I reserve half my days in Hawaii for this kind of chilling.

A Sunrise in the Sky: Haleakala, the dormant volcano at Maui’s center, is the source of much of its landside recreation and a national park to boot. One of the great experiences, while you’re still jet-lagged and waking up early, is to start the day at the top of the mountain near 10,000 feet and ride a bike down the sea-to-sky highway to the ocean. No special skills or agility required. (If you’re more ambitious, consider hiking or camping in Haleakala’s crater, then biking down the next day.) Hike Maui ( leads great hikes, and numerous operators run good downhill bike trips.

A Road Like No Other: The Road to Hana, popular as it is, is another seminal Maui experience. Fifty-two miles, 620 curves, 46 one-lane bridges, black sand (lava) beaches, and innumerable waterfalls, all ending in a peaceful former plantation town on Maui’s northern shore. Spend the night in Hana to keep the pace relaxed.

A Walk to a Waterfall: There are many secluded waterfalls along the road that circumnavigates Maui, and some are more secret than this one, but after the long drive to Hana, there is nothing better than getting out of the car, hiking a mile or so through a bamboo forest on the Pipiwai Trail, and ending up at a secluded and swimmable waterfall called O’heo Gulch. Odds are you won’t be alone, but I’ve never seen crowds here either. (Charles Lindbergh’s grave is just down the road.)

A Beachside Lunch: Hawaii is expensive, and most of us can’t afford a bespoke experience, but enjoy a sliver of the dream by lunching at Ferraro’s at the Four Seasons Resort at Wailea. It’s a truly gracious affair, even if you’re in flip-flops and board shorts. The food is great, the views sublime, and unlike many tourist traps by the water, the service and welcome are gracious and sincere.

What else? Well, this is a resort-based vacation, so the right lodging and local eating spots are key. Here are my current favorites:


Westin Ka’anapali Ocean Villas: On the northwest shore of Maui, this newer time-share resort offers a limited number of lodgings to the general public. They include multi-bedroom options with kitchens and laundries, plus all the amenities of a hotel-style resort, including spa, poolside service, and concierges. It’s very comfortable, if a tad commercial, with an unfortunate emphasis on selling guests fee-based activities. westin

Grand Wailea Resort: On the more recently developed southwest shore at Wailea, the GW is a five-star spectacle. Miles of marble, incredible artworks, gorgeous landscaping, and the big draw: a guests-only pool-waterpark that is unequaled, with appeal for kids and adults. If only it offered the food and service of the Four Seasons next door.

Travaasa Hana: Voted the number one resort in Hawaii by Condé Nast Traveler’s Reader’s Choice Awards, this small upscale resort is a sublime, if isolated, experience, offering visitors a sense of a Hawaii before large-scale tourist development. It’s high-grade but not gilded; expect a New-Agey, nature-immersed experience.


Maui has become a local-foods paradise with an endless growing season. Leoda’s Kitchen & Pie Shop: This newish, hip roadhouse in the tiny West Maui outpost of Olowalu boasts a menu of artisanal sandwiches and incredible pies for dessert. A great lunch on the way to or from the Ka’anapali area.

Cilantro: A casual Mexican counter-service eatery that was doing Chipotle one better long before Chipotle was a national presence. The perfect antidote to the $75 per person dinners so common in Lahaina.

Honu: This open-air, waterfront restaurant on Front Street in Lahaina is one of a collection of eateries owned by Maui superchef Mark Ellman. It’s all artisanal local fare, with an emphasis on seafood and wood-oven pizzas. His adjacent Mala Ocean Tavern is also highly recommended.

Flatbread Co.: This innovative and informal pizza restaurant in the surfer town of Pa’ia is a wonderful pit stop on your way to or from Hana or on a trip up Haleakala.

Hali’imaile General Store: Many Maui restaurants boast sunset views, but there’s something about the view-free dinner at chef Bev Gannon’s restored general store, “upcountry” on the way to Haleakala, that embodies the casual sophistication of the Maui experience. The foods are mostly local (fresh-caught or fresh-picked), the vibe is informal, and the experience is like no other restaurant in the state. (The nearby towns of Pa’ia and Makawao are charming local burgs free of resorts and overdevelopment and are worth a visit.)