The Ultimate Guide to Kailua, Hawaii


Oahu’s Low-key White-Sand Destination

For decades Kailua was Oahu’s local getaway, a sleepy town on the island’s windward side known for stunning beaches and a relaxed vibe. New development and an influx of visitors have brought fine dining and shopping, but Kailua’s barefoot charms endures.

When to Go

May through July, after the rainy and occasionally chilly Hawaiian winter, but before the swelter of late summer and autumn.


Kailua is popular as a get-out-of-town from Waikiki day trip. Kailua is known for its lack of resort hotels. Luckily, its just 30 scenic minutes from two of Oahu’s best: At the 338-room Kahala Hotel and Resort, located on a secluded bay east of Honolulu, a private lagoon is home to a family of bottlenose dolphins.  Guests can experience an up close and personal experience with the dolphins through the Dolphin Quest programs. The resort is also a perfect wedding destination, providing breathtaking backdrops for ceremonies and receptions. (Doubles are from $395, including a breakfast daily and a $100 hotel credit.)

The 453-room Halekulani, a quite oasis on Waikiki Beach, was one of the area’s first hotels and remains an icon-as does its orchid-emblazoned pool. It has been a Waikiki Beach landmark for more than 100 years. Enjoy swimming in the pool made up of 1.2 trillion mosaic tiles, or take a trip to the Pacific Islands inspired treatments as the SpaHalekulani.(Doubles from $525, including breakfast daily and a $100 dollar hotel credit).

Dine and Drink

For steak and local seafood or an afternoon cocktail on the lanai, Buzz’s Original Signature Steakhouse is one of the only restaurants by the beach in Kailua (it’s the oldest too). Formaggio Grill in the center of Kailua town offers Windward Oahu’s best wine selection. And don’t miss a shave ice at Island Snow near Kailua Beach Park; the frozen treats are good enough for the Obamas, who are known to drop by when they are in town.


At Mu’umu’u Heaven designer Deb Mascia brings vintage muumuus (and vintage fabrics) to stylish new life. Twin Islands is where Kailuans go for a surf-and beachwear created by local waterman Mike Miller. Hawaiian-made line Fighting Eel specializes in spare, sophisticated women’s knitwear from islands designers Rona Bennett and Lan Chung.

Best Beaches

It’s often said that Lanikai, at Kailua’s southern end, is Hawaii’s most beatutiful beach. The half-mile stretch of ultrafine sand fronts a topaz lagoon stretching toward the twin peaks of Na Mokulua, two islets easily reachable by kayak or stand-up paddleboard. Lanikai’s calm waters are ideal for swimmers and families with small kids. For a more expansive strand, head just north to Kailua Beach, which edges the town for two and a half miles.

Sunrise, Moonrise

It’s a short, steep hike to the top of Lanikai Ridge for sunrise viewing from WWll-era concrete bunkers, which locals call the “pillboxes.” Or just skip the hike and walk to Kailua Beach at dawn. Not a Morning person? Kailua’s full moonrises are just as memorable.

The Bike Factor

Kailua is small, flat, and eminently bike-able. Rent a beach cruiser and pedal around Lanikai, through Kailua Beach Park, and back to town, stopping to swim wherever you feel the urge and ending a Lanikai Juice for an acai bowel.

Give it a Try

When the winds are up, Kailua is Oahu’s premier kite-surfing beach; when it’s calm, the stand- up paddlers are out in force. Rent gear or take lessons from one of several tour operators in the town.


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