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
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.