The Windward Oahu town of Kailua—population 36,513—is only a 30-minute drive from the hustle and bustle of downtown Honolulu, but it may as well be a world away. There are Oahu residents who go for years without making the drive over to this part of the island. And to be truthful, Kailua residents are perfectly okay with that. They rather enjoy having a scenic slice of Hawaiian heaven all to themselves.
Getting to Kailua was always a challenge. Ancient Hawaiians only had two options: hiking over the Koolau Mountains or sailing around Makapuu Point along the island’s eastern shores. More often than not, they chose the direct route and climbed a trail up and over the pali (cliff). Today, most drivers reach Kailua via the Pali Highway (Route 61). No matter how rough of a day Kailua residents may have, the feeling they get as they emerge from the highway’s tunnel and take in the sweeping panorama in front of them is one of instant comfort and reverence.
Kailua is first and foremost a beach community. In fact, the steady onshore trade winds makes Kailua Beach one of the world’s preeminent windsurfing destinations. Robbie Naish, regarded by most observers as the sport’s greatest champion, grew up at Kailua Beach.
In 1998, Kailua Beach Park was named “America’s Best Beach” by coastal expert Doctor Stephen Leatherman and then “retired” from subsequent consideration. As one Kailua resident noted in ALOHA Magazine, “If I feel stressed out, boom, in three minutes I can be at the beach and rigging up my sailboard. Even if you’re not at the beach, it’s never far away. It’s in the air, you can smell it.”
Kailua is a self-sufficient town with a strong sense of community. Christmas and Fourth of July parades are held here every year. There are Little League games, block parties and canoe paddling events. For its residents, Kailua represents the good life.
“Once I come through the tunnel (from Honolulu) at the end of the day, that’s it,” said another Kailua resident. “I see Kailua and the ocean, and I’m home. I leave work on the other side.”