Image of Lanikai beach
The twin islands off of Lanikai beach. (Photo courtesy of Napua Heen)

You could describe Kailua as a typical residential area that arose from post-war development on the Windward side of Oahu. But as anyone who calls the urban side of Oahu “home” will tell you, you’re missing the point. Hugged by Mount Olomana and the Koolau Range, Kailua (meaning “two seas” or “two currents”) is a charming oceanside community filled with close-knit residents who appreciate their laid-back, outdoorsy lifestyle amid a magnificent natural setting.

Word to the wise when visiting this town — come hungry, as there is definitely no shortage of sweet and savory “Perched atop the pillboxes on the Lanikai Ridge, I am reminded of all the things I have had the opportunity to experience while living in Hawaii,” says 25-year Kailua resident Alison Ritson. “With the cool trades fanning me, I look out at the ocean currents as far as I can see and am reminded of my outrigger paddling and steering that I have been a part of for 13 years.”

Whether paddling canoes or kayaking, windsurfing or just soaking up the sun, families of locals and tourists alike regularly make a splash at Kailua Bay, which has been rated as one of the world’s best beaches by numerous publications. “Just beyond Popoia Island (also known as Flat Island) are some of my favorite scuba and snorkel spots that I have visited with my family,” Ritson says.

In addition to ocean adventures, Kailua boasts breathtaking trails and hikes. The pathway along Kawainui Marsh, for instance, is a favorite local spot for biking and jogging. The trail wraps around a vast wetland, offering reminiscent views of a nourishing space once used by Kailua’s earliest residents for farming and sustaining fishponds.

Image of Rasa Fournier
(Photo courtesy of Rasa Fournier)

Hikers also love to venture to a corner of the beach community named Lanikai, to follow the Pillbox Trail up Kaiwa Ridge for a stunning view of the Mokulua Islands off Lanikai Beach.

After an exciting outdoor excursion, the best way to cool down is to stroll around town, visiting the many mom-and-pop shops as well as one-of-a-kind restaurants that give Kailua its unmistakable warmth. A bountiful of boutiques, surf shops and specialty stores make it the perfect place for some relaxing retail therapy.

With a refreshing ocean breeze swirling through the neighborhood, Kailua remains everybody’s favorite beach-town escape.

Good eats around town

Along with an array of local boutiques, Kailua gets its homey feel from a slew of unique eateries, including:

  • Kalapawai Market. This specialty grocer and deli has served the community at the entrance to Kailua Beach Park since 1932. The market recently branched out by opening Kalapawai Cafe in the heart of Kailua town, showcasing yummy eats and local art.
Image of Kalapawai market
A couple enjoys a refreshing snack outside of Kalapawai Market. Photo courtesy of Hawaii Tourism Authority (HTA) / Daeja Faris.
  • Casablanca. For a taste of Kailua’s diversity, try authentic — and mouthwatering — Moroccan cuisine at Casablanca.
  • Morning Brew. Brewing up fresh coffee, espresso and teas, this delightful coffee house and bistro serves the best in baked goods and scrumptious breakfast options perfect for lazy mornings.
  • Buzz’s Steak House. Head to Buzz’s, located by the beach at the foot of Lanikai, for some great surf and turf with a local twist.