Kailua

 

Frequently ranked one of the most desirable communities in the Hawaiian Islands, Kailua is a picturesque, quintessential beach town situated on Oahu’s gorgeous windward coast. Located roughly 20 minutes away from “town” (or the stunning metropolis that is Honolulu), the small city once served as an oasis for Hawaii’s loyalty. Understandably so because, between its views of the verdant Koolau mountains and its stretches of immaculate white sand beaches, Kailua contains all of the elements that earned Hawaii its legendary status.

 

Kailua preserves its vacation feel but with an important caveat: There are no immense resorts on its majestic beaches, no towering skyscrapers, and no massive shopping plazas. Instead, you’ll find a panoply of both kick-back and opulent restaurants, cozy coffee houses, bustling neighborhood markets, shave ice stands, and unique, independent boutiques showcasing the work of Hawaii’s finest entrepreneurs. The homes here mirror Kailua’s understated sophistication, with spacious, airy estates featuring koa wood details, lush landscaping, and booming views of the Pacific. And yet, Kahala’s casual nature — a place where you can go anywhere in your surf shorts and slippers — gives it a fun, old-school Hawaii feel that makes every day downright idyllic.

 

• A tranquil, suburban, tight-knit vibe
• Proximity to downtown Honolulu, Waikiki, and the North Shore
• Excellent for walking and biking around town
• Minutes away from a bounty of awe-inducing hikes
• Home to two of Hawaii’s most exquisite beaches

The beauty of Kailua is that it calls to a wide range of residents. Affluent professionals who enjoy being a short commute away from Honolulu? Check. Retirees who relish time in the surf and sand? You bet! Passionate artists and entrepreneurs inspired by Kailua’s quiet and beauty? Of course. The aloha-spirited residents that make up Kailua give it its irresistible soul. You’ll often run into your neighbors on Lanikai or perusing the goods at the local farmers’ market.

 

Honolulu may be a mecca for foodies, but Kailua comes in at a very close second, with great thanks to its high concentration of superb eateries, many of them helmed by the most prominent chefs in Hawaii, and its terrific, locally-owned venues.

 

To wit: Kalapawai Cafe & Deli. This lively eatery, nestled inside a historic home, features a vast assortment of fresh produce, delicious sandwiches, irresistible salads, and beloved local treats. It is a top spot for a relaxed dinner under the stars or to pick up supplies before picnicking on the beach. Buzz’s Original Steakhouse has been a perennial favorite for Oahu residents since its inception in 1962. Located on the beach with a definitively tropical feel, this is a go-to spot for awesome surf-and-turf and mai tai-infused special occasions.

 

Many of Kailua’s residents are early risers — who would want to miss out on a minute of Hawaii’s perpetually splendid weather? — and they often head to Cinnamon’s Restaurant Kailua to fuel up for the day. Guava chiffon pancakes, macadamia nut cinnamon rolls, and shoyu pork belly loco moco are just a few of the selections you’ll find on Cinnamon’s delicious menu. Boots & Kimo’s Homestyle Kitchen is also often abuzz with Kailua residents, who savor hearty breakfasts like banana macadamia nut pancakes and homemade fried chicken and waffles. Regardless of your craving, Kahala is sure to satisfy. 

 

Kailua’s prime location on the windward side of the island means its residents are perfectly positioned to enjoy an array of activities within minutes. Lanikai and Kailua Beaches, which are consistently ranked two of the world’s most magnificent beaches by Conde Nast Traveler, offer terrific conditions for swimming, snorkeling, SUPing, and kayaking to “The Mokes,” a pair of isles just off the coast.

 

Kahala’s strong community feel is underscored in events and activities throughout the year. Kailua Farmer’s Market is a local treasure with its collection of vendors peddling everything from organic honey to malasadas. The Kailua Art Fair in downtown Kailua is equally cherished. Its annual parades, including a vibrant Christmas parade, and a spirited 4th of July extravaganza, lure people to the town’s lush, pristine streets.

 

Kailua is home to a handful of top-performing schools, such as: