How to take a World’s Best trip to Maui.

The Trip

Within the Hawaiian-island family, Maui is the celebrity sibling: radiantly beautiful, a bit rebellious, and with glamour to spare. The island has attracted “seekers” for its healing energy since the 1960’s and, more recently, Internet millionaires and Hollywood A-listers who want to rejuvenate in five-star spas. Glossy Wailea, in the south, is home to the Maui Film Festival every June—your best bet to hobnob barefoot with Kristen Bell or Zac Efron—and culinary destinations such as chef Peter Merriman’s new Monkeypod Kitchen, a showcase for local beef and produce. Even more cosmopolitan is the North Shore, where transplants from Paris, New York, and São Paulo are putting down roots. In Paia, a town with an organic-chic vibe, surfer Laird Hamilton follows a session of riding giants with some Maui-roasted coffee at Anthony’s Coffee Co. Pick up a pizza topped with local chèvre at Flatbread, or try on a floaty island-style dress from Argentine designer Tamara Catz. From here, the drive to Hana, on the eastern side of the island, takes two hours but brings you back 50 years, to the Maui of secret waterfalls, empty beaches, and pervasive spirituality—with nary a high-rise in sight.

Maui Active Tip: Hana’s Oheo Gulch, a series of waterfalls and ponds also known as the Seven Sacred Pools, is protected thanks in part to Laurance Rockefeller, who donated a portion of the surrounding land to the National Park Service. Once you’ve dried off, consider tackling the forested Pipiwai Trail, one of Maui’s most scenic.

Related: The Best Beaches in Hawaii

Maui Family Tip: The kids will catch a wave right away with a lesson in stand-up paddling, a gentler alternative to surfing that uses an oar and a big board to help with stability. North Shore–based Stand-Up Paddle Boarding School is dedicated to the pursuit. 808/579-9231; lessons from $159 per person.

Maui: World’s Best Scorecard

No. 9 island overall
No. 3 island in Hawaii

Hotels

Four Seasons Resort Maui at Wailea 92.15
Travaasa Hana (formerly Hotel Hana-Maui & Honua Spa) 91.53
Ritz-Carlton, Kapalua 88.63
Fairmont Kea Lani 88.26
Hyatt Regency Maui Resort & Spa 88.20
Grand Wailea Resort Hotel & Spa 87.13
Wailea Beach Marriott Resort & Spa 86.22
Sheraton Maui Resort & Spa 86.21

Related: Things to do in Maui

Anthony’s Coffee Co. 90 Hana Hwy., Paia; 808/579-8340; anthonyscoffee.com; espresso for two $4.

Flatbread 89 Hana Hwy., Paia; 808/579-8989; flatbreadcompany.com; dinner for two $35.

Maui Film Festival 808/579-9244; mauifilmfestival.com; June 5–19, 2012; day passes $22.

Monkeypod Kitchen 10 Wailea Gateway Place, Kihei; 808/891-2322; monkeypodkitchen.com; dinner for two $100.

Tamara Catz 83 Hana Hwy., Paia; 808/597-9184; tamaracatz.com.

Sheraton Maui Resort

Kaanapali's first resort claims Maui's best ocean setting. And that means beach activities from morning dives to astronomer-led stargazing.

Wailea Beach Marriott Resort & Spa

All the classic resort amenities, plus koi ponds, old-growth banyan trees, and other authentic Hawaiian details are par of this mahogany-and-rattan chic property on Maui's ruggedly beautiful south shore. The luau here is one of the island's most authentic.

Hyatt Regency Maui Resort & Spa

At the southern tip of Ka'anapali Resort and only two miles from Lahaina, the Hyatt Maui is an exceptional property—and exceptionally difficult to leave. After all, with the best pool system in Ka'anapali and a Grotto Bar under a waterfall, it's easy for families, couples, and groups to lounge all day by the pool. When the sun sinks down behind Lana'i, savor a dinner of hand-rolled sushi at the resort's restaurant, Japengo, or enjoy dinner with a fire-and-knife show at the Drums of the Pacific Luau. For a romantic, educational, and mesmerizing evening, head to the rooftop for the Tour of the Stars, where a 14" telescope and cultural guide help you scour the Polynesian sky.

Travaasa Hana

Travaasa is Maui's original resort, having opened its doors in 1946 in the most peaceful corner of the island. This is where luxury, simplicity, and beauty are fused with Hawaiian culture; resort activities include fishing with throw-nets and cooking regional cuisine. Unwind at the unparalleled Spa at Travaasa, or enjoy an evening of authentic Hawaiian music in the Paniolo Lounge. The ocean bungalows are like private cabins with Pacific views, and a private jacuzzi embedded in each deck invites a sunset soak. Since the resort is located all the way in Hana, it's far away from everything—which is exactly where you want to be to unwind, untether, and escape.

Ritz-Carlton Kapalua

There isn’t a moment on this Ritz-Carlton property when you don't feel like royalty. From the spacious rooms to the opulent spa to the enormous, three-tiered pool, everything here is topped off with an exquisite air of grandeur. As an added bonus, Kapalua has some of the island's best golf, tennis, and snorkeling.

Fairmont Kea Lani

Every room in this whitewashed resort is a large, comfortable suite, and the fusion of Hawaiian and Mediterranean ambience creates a classy feel throughout. The resort is one of the island's leaders in eco-sustainability, and to really feel like a rock star for a night, book a two-story oceanfront villa with a private outdoor pool.

Grand Wailea, a Waldorf Astoria Resort

Whether it's splashing in Maui's best swimming pool all day or relaxing in Maui's best spa, a day spent at the Grand Wailea is synonymous with island luxury. In recent years, the Grand Wailea has led an exciting hyper-local food movement, where many of the resort's food and beverage items are grown or harvested on Maui. A few items, such as resort-grown honey, are sourced right on the property, and there's even a monthly dinner featuring food caught or harvested by hotel staff. Oh, and the 780-room property is set right on Wailea Beach—which in 1999 was voted by "Dr. Beach" as the #1 beach in America.

Four Seasons Resort Maui at Wailea

There's a fairy-tale magic emanating through this award-winning Wailea resort, where elegance, opulence, and impeccable service create a sumptuous aura of luxury. After basking poolside in a cream-colored cabana or a 5,500-square-foot suite, you can spring for a soothing massage treatment in the ultra-luxurious spa.

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