“The minute I come over the mountains and see Kailua down below,” says resident Matt Rosete, “I start to feel relaxed.”
Kailua, the town of 38,600 on windward Oahu, has that effect on people. Walled off from Honolulu by the corrugated cliffs of the Koolau Range, Kailua has none of the dazzle of touristy Waikiki—no hotel towers, ultra-lounges, or high-priced shopping opps. Instead, it offers the blood pressure–lowering pleasures of an unpretentious small town, but one with a supremely blissful, tourist-free setting.
The setting stretches out along Kailua Bay, with three cartoon-looking islands—Flat and the Mokuluas, or “twin islands”—floating just offshore. Kailua Beach Park, toward the bay’s southern end, regularly garners awards as one of Hawaii’s top beaches, but nearby Kalama and Lanikai are just as good—some would say better.
In past centuries, Kailua’s beaches and beauty drew vacationing Hawaiian royalty, but these days the town is pleasantly eclectic. “It’s a real hodgepodge,” says Sheila Lou Rosete, who with husband Matt opened ChadLou’s Coffee & Tea Lounge downtown two years ago. “There’s a military presence”—from Marine Corps Base Hawaii, just to the north. “Plus families that have been here two or three generations, and newcomers looking for their piece of paradise.”
The atmosphere is low-key. Except for open-stage events at ChadLou’s, there’s not much nightlife. But there’s a great twice-a-week farmers’ market. No hotels, but you can find homes and condos to rent. No four-star dining, but enough bistros and cafes to satisfy the ex-urbanites who now commute to work in Honolulu, and a terrific shave-ice stand.
These pleasures—and, of course, the beaches—give Kailua a strong gravitational pull: Once people visit, they start thinking about a second trip, or a third. The most famous returnee is President Barack Obama, who spent time here as a child and who has visited regularly on First Family vacations.
But regular folks feel Kailua’s pull too. Matt was raised here, then attended college in California, where he met San Diego native Sheila Lou. They’ve returned to raise their own family—two kids, a third due this month. “It’s the kind of place,” she says, “where you walk down the street and admire somebody’s garden and end up talking to them for a half-hour. I always knew that we’d want to come back.”
Next: What to do and where to eat
Your perfect Kailua day
Bike it. Flat and compact, Kailua is made for exploring by two wheels, though weekend traffic can be busy. Bike share B-cycle (hawaii.bcycle.com) gives you 24-hour access to a bicycle for $5 plus usage fees. Another option: the Bike Shop (from $20/day; bikeshophawaii.com).
Coffee and culture. Grab a latte, admire custom skateboards, and hear local music at Sheila Lou and Matt Rosete’s ChadLou’s Coffee & Tea Lounge. 45 Kihapai St.; 808/263-7930.
Get elevated. The short (1 mile one way) but steep Lanikai Pillbox Trail takes you up to World War II–era bunkers and an Imax-worthy view of windward Oahu. The trailhead is across from the Mid Pacific Country Club (266 Ka‘elepulu Dr.; mpcchi.org).
Juice up. Kailuans love Lanikai Juice, where the smoothies are made with local papaya, passion fruit, and pineapple. 600 Kailua Rd.; 808/262-2383.
Brain freeze. Cool down with shave-ice at Island Snow, just a five-minute walk from Kailua Beach Park. 130 Kailua Rd.; 808/263-6339.
Beach time. The calm surf at Kailua Beach Park (21 S. Kainalu Dr.) is made for kayaking and stand-up paddleboarding; you can rent gear at Kailua Sailboards & Kayaks (kayaks from $39/half-day, boards $49/half-day; kailuasailboards.com) and at Twogood Kayaks Hawaii (kayaks from $45/half-day, boards $39/half-day; twogoodkayaks.com). For more bodysurfing-friendly waves, try nearby Kalama Beach Park (248 N. Kalaheo Ave.) and Lanikai Beach (Mokulua Dr.).