Kailua is the country cousin of Oahu's glossy but overbuilt Diamond Head-Waikiki Gold Coast. It's what the whole island was like 40 years ago, when coconut trees, rather than high-rises, dominated the skyline. There are still no hotels in town, and the most popular hangout is the beach. Studded with palms and ironwoods, it stretches for four miles and has some of the softest sand anywhere—white and talcum-powdery and perfect for sandcastles (but good luck getting it out of your hair). Head "mauka"—toward the mountains—and you'll run straight into the emerald curtain of the Koolau Mountain Range,where trails lead to waterfalls and forests laden with ginger and passion fruit. As if all that weren't enough, Kailua is also rich in Hawaiian history. King Kamehameha I fought a decisive battle here to unite the islands, and several heiaus, or open-air temples—some of them once used for human sacrifice—sit near the Kawai Nui Marsh.
Probably 95 percent of the people you'll encounter in Kailua will be Oahu locals. Outsiders rarely make it over the mountains, unless they're windsurfers in search of some of the state's best rides. So the next time you're on the island, be a trailblazer. Here, an insider's guide to point you in the right directions.
LAY OF THE LAND Greater Kailua extends from the Koolaus to the sea on the windward side of the island. Though the mountains are seductive, they can attract clouds and rain. Book a place "makai"—on the ocean side—of Kalaheo Avenue. This will put you within a short walk of Kailua Beach.
STANDOUT BEACHES Kailua Beach Park is beautiful, and practical, with bathrooms and showers on-site. In search of something more untouched?Head straight to Lanikai Beach.
DON'T MISS The cliff-top panorama and whipping wind at the Nuuanu Pali lookout. And on Friday and Saturday nights, go "cosmic bowling" at Pali Lanes (120 Hekili St.; 808/261-0828), where, after nine, the disco ball and laser lights are on and the bowling balls glow in the dark.
RENT FROM Trinity Properties (808/247-7521; www.trinityproperties.com) or Bradley Properties (808/734-2000; www.bradleyproperties.com). Weekly rate for a two-bedroom cottage near the beach: $1,500 and up. B&B's in Kailua tend to be separate cottages or apartments on the owner's homesite and cost $45 to $150 a night. To find one, contact Affordable Paradise (808/261-1693; www.affordable-paradise.com).
ESSENTIAL EATING Locals swear by the pulehu (char-grilled) short-rib breakfasts at Boots & Kimo's Homestyle Kitchen (131 Hekili St.; 808/263-7929; breakfast for four $40). For dinner, check out Pinky's Pupu Bar & Grill (970 N. Kalaheo Ave.; 808/254-6255; dinner for four $40). It's decorated in kitschy Hawaiiana and has a long pupu menu (perfect portions for kids).
IDEAL OUTING Down the road in Waimanalo, visit Sea Life Park (41-202 Kalanianaole Hwy.; 866/365-7446), a Hawaiian take on Sea World, where the dolphins do the hula.
PERFECT SOUVENIR A hula-girl dashboard figurine from Under a Hula Moon (600 Kailua Rd.; 808/261-4252). Or a Hawaiian toile duvet cover from Delano & Seymour's Hawaiian House (602 Kailua Rd.; 808/263-1033).
REQUIRED FOOTWEAR A $2.99 pair of rubber zori (flip-flops) from Kalapawai Market & Deli (306 S. Kalaheo Dr.; 808/262-4359).
LOCAL LINGO Mahalo means "thank you"—one of the best words to learn in any language.
MALIA BOYD grew up on Oahu. She writes for Travel + Leisure and Food & Wine.