Vibrant and unpolished, this one-stoplight town on Maui’s breezy north shore has willfully remained in a time warp from the days when King Sugar ruled the island. Home to California escapees and an international mix of year-round beach bums, Paia (pronounced pa-ee-a) has lately become a windsurfing mecca—with a serious celebrity quotient. Surfing hero Laird Hamilton holds court at Anthony’s Coffee Co., and Willie Nelson, a sometime resident of the Valley Isle, occasionally swings by the juke joint Charley’s and plays a guest set—not that anyone in this determinedly low-key outpost bats an eye. Sound enticing?Pull on surf trunks and "rubber slippahs" (as flip-flops are known in these parts), and you’ll fit right in.
Lay of the Land
Paia sits surrounded by waving fields of sugarcane and pineapple. Low-slung storefronts painted in pastels line Baldwin Avenue and the Hana Highway, the main drags that meet in the center of town. Paia’s gathering place is Baldwin Beach Park, an impressively long strand just east of the center, where everyone strolls along the surf and barbecues at sunset. Spongers (bodyboarders) don their fins and drop in at favorite breaks, while keiki (children) splash in Baby Beach, a reef-protected lagoon on the park’s far eastern end.
What to Do
To catch a glimpse of Laird and his crew slingshotting into 60-foot waves, grab some binoculars and drive just north of Hookipa Beach Park, to the cliffs that overlook the legendary surf break called Jaws. Crowds line the precipice to ogle tow-in surfers as Jet Skis pull them into the massive swells. In the park itself, you can watch wave-jumping (surfing and jumping over waves on a sailboard) and kite surfing (like windsurfing, except a large kite pulls you)—and explore the tide pools yourselves. Kids can learn to windsurf at nearby Kanaha Beach Park, where HST Windsurfing and Kitesurfing School (425 Koloa St., Kahului; 808/ 871-5423; hstwindsurfing.com) runs year-round three- and four-day kids’ camps (from $199).
Where to Stay
There are no big hotels or condos in Paia, and everyone likes it that way. Mama’s Fish House (799 Poho Place; 808/579-8488; mamasfishhouse.com; from $225 per night), a 34-year-old eternally packed restaurant, known for its fresh-caught opakapaka and opah cooked Tahitian-style, has nine somewhat secret rental cottages with covered lanais right on Kuau Cove. Other vacation rentals are available—but be warned that Maui County has recently begun to shutter properties that lack an official permit. Inquire about legalities before you book. Two agencies to try: Hawaii’s Best Rentals (866/772-5642; hawaiisbestrentals.com) and Chameleon Vacation Rentals Maui (866/575-9933; donnachameleon.com). The latter’s three-bedroom Hale o ke Kai (House by the Ocean), a stroll away from the lovely, calm beach surrounding Mama’s, is $225 a night.
Where to Eat
For giant pancakes with coconut syrup, go to Anthony’s Coffee Co. (90 Hana Hwy.; 808/579-8340). Or head 20 minutes up the hill to T. Komodo Bakery & Store (3674 Baldwin Ave.; 808/572-7261) in the cowboy town of Makawao; if you’re not in time to nab custard-filled cream puffs—they often sell out by 7:30 a.m.—you’ll be more than consoled by their "long-john" doughnuts. At lunchtime, locals jam the Paia Fish Market Restaurant (100 Hana Hwy.; 808/579-8030; lunch for four $40) for the tastiest fish burgers and tacos on the planet. The place for dinner, when you’re not splurging at Mama’s, is the Flatbread Company (89 Hana Hwy.; 808/579-8989; dinner for four $60) for wood-fired pizza. Get your groceries and picnic fare at Mana Foods (49 Baldwin Ave.; 808/579-8078), a health-food store with a prime selection of Maui-grown pineapples and strawberry papayas—and the island’s best-looking clientele.
Dad can slip on a pair of Maui Rippers board shorts at Simmer Hawaii (137 Hana Hwy.; 808/579-8484). Bikini-wearing moms get outfitted at the chic flagship store of Argentinean designer Tamara Catz (83 Hana Hwy.; 808/579-9184), whose husband is windsurfing world champ Francisco Goya. Hana Hwy Surf (149 Hana Hwy.; 808/579-8999) sells its own brand of junior trunks ($39). Before taking off, lay in a supply of Maui Gold pineapples—available boxed to go at the Kahului Airport—so you can continue the luau back home.
Oahu-based Alex Salkever, a father of two, writes the travel blog Hawaiirama.com.