Dream Town: Kailua, Hawaii
The Ultimate Beach Town?
There are beach towns, and then there’s a town so stop-in-your-flip-flops gorgeous, it’s tempting to name that place the ultimate beach town. Such is the temptation of Kailua, Oahu’s slender strand along its windward shore that’s home to two idyllic public beaches and 53,000 very lucky Hawaiians.
Surrounded by steep emerald slopes and carved quietly by rivers that flow into Kailua Bay, this understatedly hip community just 12 miles from Honolulu is endowed with extraordinary beauty, a serene lifestyle, small-scale neighborhoods of single-family homes, a walkable downtown with great food and shopping, and vistas without peer (even in Hawaii, where paradise comes with the ZIP code).
Small and Creative Community
Locals maintain a tight leash on development, and the result is a downtown that’s small in scale and big on community (and has a median home price of $918,000). Here, surf-inspired boutiques, an electric-bike shop, and an artisan chocolate factory founded by young local entrepreneurs now keep company with traditional businesses including an old-school bowling alley, a pancake house, and a dive shop.
What hasn’t changed in Kailua is its laid-back style, says Cynthia Manley, who moved here from Virginia to give her daughters a small-town upbringing full of paddling at the beach and pedaling into town for shave ice. “Now,” she says, “we’re more like a paradise within a paradise.”
On the northern end of Kailua, Kailua Beach arcs in powdery white-sand splendor for 2 1/2 miles. The gentle ocean drop-off from shore makes it perfect for swimming, bodysurfing, and surfing, and a steady trade wind also makes it ideal for windsurfing (no wonder Kailua spawned the sport’s youngest world champion, legend Robby Naish).
While small roads grant access to the shore, visitors love Kailua Beach Park, a convenient base with parking, shady groves of ironwood trees, and nearby vendors renting all kinds of watercraft. Even more pristine than its sibling, mile-long Lanikai Beach has crystalline waters. Don’t miss the view here of moonrise behind the famed Na Mokulua Islands, better known as the Mokes.
And while Kailua’s best-known vacationer (hint: he’s the President of the United States) may be loyal to Island Snow for shave ice, the oversize confections at The Local infuse mega snowballs with all-natural syrups (from local star Ono Pops) in flavors like mango, ginger, and tamarind. This is the future of shave ice, and it’s glorious.
Eat and Drink
Revel in a vintage Hawaiian zeitgeist by finishing your beach day at Buzz’s Original Steak House. Kailua’s only waterfront restaurant is the home of a wicked house mai tai—an all-rum trifecta of Bacardi light and dark with a float of Myers’s. For fresh catch and crafted cocktails, the plantation-style Kalapawai Café and Deli fills with locals who know to grab the shaded patio tables early in the evening. Don’t miss the Kalapawai Market (pictured) near the beach, for hearty espresso, creative sandwiches, and people watching.
Shop: Fighting Eel
For original designs that go from beach to brunch (and beyond) Fighting Eel spotlights sophisticatedly relaxed pieces designed by owners Rona Bennett and Lan Chung under its own brand, plus Bennett and Chung’s second line, Ava Sky.
Manuheali’i is a color-filled cottage where husband-and-wife designers Pono and Danene Lunn introduce a new patterned fabric every four to six weeks for their maxis, tunics, and traditional shirts. Which is a reason to return to Kailua every other month (or just plain move there).
Shop: Splash Hawaii
Call them “slippers,” as Hawaiians do, and then fall in love with hundreds of colorful flip-flops and sandals at Splash Hawaii. They fill the walls, and you'll be hard-pressed not to walk out with several new pairs. Splash also carries local brands of bags, hats, and very cool t-shirts.
Because Kailua strives to stay largely residential, the in-town overnight scene is more limited than most Hawaiian destinations. For a resort stay, Paradise Bay Resort in neighboring Kaneohe is a low-key gem with studios, suites, cottages, and stunning views across Kaneohe Bay to the lush palisades of the Koolau Range. Rates start at $199; paradisebayresort.com.
For a destination escape less than an hour away on the North Shore, the recently reimagined Turtle Bay Resort has luxuriously appointed cottages, a cool surf-themed bar, a top- notch spa, and activities ranging from surf and SUP lessons to horseback riding and golf. Rates start at $279; turtlebayresort.com. Read about our Travel Editor's trip to Turtle Bay, here.