Over the past two decades, Kailua has transformed from a tranquil neighborhood to a buzzing beach town, complete with a Whole Foods Market, Target, and soon, Maui Brewing Co. in a newly developed shopping complex along Kailua Road. Kailua has become one of the hottest, and most expensive real estate markets on the island. But the Windward town still retains is oceanside community charm; there aren’t clusters of high-rises or large cookie-cutter neighborhoods here. Most Kailua residents have called the Windward town community for the majority, if not the entirety of their lives. Kailua town has a smattering of local boutiques and eateries, including the popular Cinnamon’s Restaurant and Boots & Kimo’s Homestyle Kitchen, both renowned for their fluffy, flavored pancakes, Kalapawai Market, the perfect post-beach or hike place for sandwiches and Island Snow for shave ice. Its beaches and parks are the perfect place to relax on the weekends. There’s a reason former President Barack Obama and his family stayed in Kailua each winter during the holidays!

Kailua Beach Park

When most people close their eyes and envision Hawaii, a long stretch of white sand appears, gentle turquoise-hued waves tickling your toes. That vision is a reality with Kailua Beach Park. It’s the tropical paradise for which nearly 5.5 million people visit Oahu each year. It’s also consistently rated one of the best beaches in America by geoscientist and coastal ecologist Stephen Parker Leatherman, more commonly known as Dr. Beach. Sheltered by Kailua Bay, the waves are calm, making it great spot to standup paddleboard, swim, snorkel or bodyboard. Kailua Beach Park is a great beach for families; it’s common to see the whole ohana, or family splashing in the water, camped beneath a shade tent or picnicking at one of the park’s picnic-table pavilions. The bay is even home to three offshore islets, Popoia, or Flat Island and the twin Mokuluas. All three are easily accessible via kayaks and a great way to spend the afternoon. Paddlers have been known to spot a honu, or green sea turtle along the way!

I Love Kailua Town Party

Kailuans are passionate about their town, its unique charm and its surrounding natural beauty. So much so, that in 1992 they started a festival honoring Kailua. This annual community festival says it all in the name—I Love Kailua. After seeing this festival in action, chances are you’ll feel the same, too. It’s one of Windward Oahu’s biggest festivals and in 2017 it celebrated its 25th anniversary. The I Love Kailua Town Party is a fundraiser organized by the Lani-Kailua Outdoor Circle. The festival is a block-party that takes places in the heart of Kailua town—the streets are closed to car traffic—and offers something for everyone in the family, and pets, too. Dozens of Kailua-owned businesses set up booths selling fresh made food, locally made jewelry, home decor accessories and clothing. Don’t miss the popular, “I Love Kailua” logo booth, which sells limited edition apparel and accessories designed annually by Kailua artists. There’s also live music from popular local musicians and hula performances. What’s not to love? 

Lanikai

In the 1920s, well-heeled kamaaina made the journey from Honolulu to Kailua in Ford Model Ts on the recently expanded Pali Road. At the time, Kailua’s small beach community, known today as Lanikai, was merely a windswept hillside. But the area had much to offer and its beauty was immediate to all those who saw it. Spectacular views of the twin islets, the Mokuluas can be had from the mountain top, not to mention the tranquility of powder-fine Lanikai Beach below. In fact, the name Lanikai loosely translates to “heavenly sea.” It wasn’t long after Honolulu businessmen first started driving north that the area was developed. In 1924, Lanikai, known to Hawaiians as Kaohao, became incorporated. Two years later, a handful of Honolulu businessmen opened the Mid-Pacific Country Club, one of Oahu’s most prestigious private golf courses. Today, Lanikai is a vibrant neighborhood of civic-minded homeowners who work not only to preserve the neighborhood, but also its world-class beach and its green spaces. Notable community events throughout the year include, twice yearly theater plays by the Lanikai Mortgage Players, the semi-annual Lanikai Craft Fair and the annual Lanikai Woes Day Parade, celebrating all things Lanikai.
Cori’s Tip: For a perfect evening in Lanikai, visit Buzz’s Lanikai—a tiki-themed steakhouse known for its kiawe-grilled teriyaki steak—then go for a stroll on the powdery white sands of Lanikai Beach. 

Mokuluas

Mokulua Iki and Mokulua Nui, known collectively known as the Mokuluas, are Oahu’s most popular offshore islets. Meaning “two islands,” the Mokes, as they have been affectionately dubbed, are frequently photographed and reproduced by local artists. But you can also paddle out to Mokulua Nui, the larger of the twin islets. There are several companies in Kailua town that rent kayaks for affordable half-day or full-day rates. And since the waters are calmer thanks to the shape of Kailua Bay, a kayak trip is easy and fun. Be sure to keep an eye for honu, or green sea turtles, too! The islet has a small beach, perfect for a post-paddle lunch. Around the backside is a small cove and tide pool called Queen’s Bath. It’s also a great spot to view Mokulua Nui’s twin, Mokulua Iki. Cori’s Tips: Paddle out to Mokulua Nui on a weekday—commercial vendors also don’t rent kayaks on Sundays. Admire the Mokuluas from a distance, too. From Kailua or Lanikai beach parks, you have a picture perfect view of the islets and from here you watch the sun set. Even better, visit during a full moon. 

Lanikai Pillbox Hike

The Kaiwa Ridge Trail, more popularly known as the Lanikai Pillbox Trail has become one of Oahu’s most popular hikes. Each weekend, hundreds of people make the trek up the roughly one-mile hike rising above Windward Oahu. The intermediate trail provides hikers with beautiful vistas of Lanikai, Kailua, the Koolau Mountains, Waimanalo, and out to the sea, the Mokulua islets. The hike gets its colloquial name because of the two pillboxes perched at the top of the hill along the windblown ridge, even though technically the structures were used as observation stations during World War II. (A pillbox is a defensive station, which typically houses a machine gun.) But although the concrete buildings have long since been decommissioned, they provide the perfect spot to take photos, and rest. The hike itself takes about an hour, depending on how many photos you take atop the two pillboxes! The trailhead is on the road to the left of Kaelepulu Drive, just before the neighborhood’s gated community and across from Mid-Pacific Country Club. Cori’s Tips: Hike the Lanikai Pillbox Trail on a weekday in the early morning or late afternoon. Park on Kaelepulu Drive, or the nearby streets and be sure to respect the neighborhood’s residents. Don’t forget water and sunscreen, and leave Fido at home; this isn’t a great hike for pets.