Discover beachfront stays, homestyle eats, and local boutiques in this impressively tranquil town
Kailua, the town of 38,600 on windward Oahu, has an incredibly relaxing 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 that’s worth a visit.
WHERE TO EAT
Lanikai Juice. Kailuans love this local juice shop, where smoothies are made with local papaya, passion fruit, and pineapple. $; 600 Kailua Rd.; 808/262-2383.
Island Snow Cool down with shave-ice at Island Snow, just a five-minute walk from Kailua Beach Park. Come for the cool treats, stay for the surfing accessories like board shorts and sunglasses. $; 130 Kailua Rd.; islandsnow.com or 808/263-6339.
Uahi Island Grill. Enjoy home-style appetizers and entrees, ranging from Kalua pig french fries and garlic ahi to orange glazed duck and poke. $$; 131 Hekili St. #102 uahiislandgrill.com or 808-266-4646.
Agnes Portuguese Bake Shop. Craving a sweet treat? Look no further. These fried, sugary donuts are a known Portuguese treat. The bakery also serves a multitude of pastries–just take your pick. $; 46 Hoolai St.; 808/262-5367.
The Hibachi. Deemed poke heaven by local patrons, this casual eatery is a must for seafood lovers. $$; 515 Kailua Rd; 808/263-7980.
Buzz’s Original Steakhouse. Visitors craving juicy steaks, barbecue ribs, and teryaki burgers can stop by Buzz’s for hearty meals and fresh seafood. $$$$; 413 Kawailoa Rd, buzzsoriginalsteakhouse.com or 808-261-4661.
Cinnamon’s Restaurant. Ingulge in guava pancakes and kalua pork omellettes at one of Kailua’s bustling breakfast joints. $$; 315 Uluniu St.; cinnamons808.com or 808/261-8724.
WHERE TO STAY
Lilikoi Cottage. Due to the town’s lack of hotels, guests get a localized experience through neighborhood vacation rentals. This stylish 2-bedroom cottage is just one of Airbnb’s options, offering all the essentials and a supreme location-just one block from the beach. $; Airbnb.com
Papaya Paradise. This quiet, simply furnished bed and breakfast comes with private entrances, wifi, and views of Mt. Olomana. $; 395 Auwinala Rd.; windward-oahu.com or 808/261-0316.
Lanikai Bed & Breakfast. Take your pick between two beachfront vacation rentals and a cozy one-bedroom suite just a few blocks away from Kailua Beach Park. $; lanikaibeachrentals.com or 808/261-7895.
Kailua Guesthouse. While quaint, this well-kept beach bungalow offers mountain views and a convenient location just ten minutes away from Kailua Beach. $; kailuaguesthouse.com or 888-249-5848
Paradise Bay Resort Less than ten miles from Kailua in Kaneohe Bay, this resort hosts sumptuous suites, private cottages, and breathe-taking views of the Koolau Mountain range. $$$; 47-039 Lihikai Dr., Kaneohe; paradisebayresort.com or 800/735-5071.
WHAT TO DO
Bike Shop. Flat and compact, Kailua is made for exploring by two wheels, though weekend traffic can be busy. Rental your own at this local shop. $$; 270 Kuulei Rd.; bikeshophawaii.com or 808.261.1553.
ChadLou’s Coffee & Tea Lounge. Grab a latte, admire custom skateboards, and hear local music at Sheila Lou and Matt Rosete’s local gathering spot. $; 45 Kihapai St.; 808/263-7930.
Lanikai Pillbox Trail. The short (1 mile one way) but steep hike 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.
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).
Lanikai Beach. Kailua Beach Park isn’t the only option for ocean lovers. Those looking for a different scene can scope out more bodysurfing-friendly waves just a mile south. $; Mokulua Dr.
WHERE TO SHOP
Lanikai Bath and Body. A sun-kissed tan isn’t complete without proper skin rejuvenation. Treat yourself to Hawaiian Mineral salts or one of the many body butters made from natural, local ingredients. $$; 600 Kailua Rd.; lanikaibathandbody.com or 808/262-3260.
Sweet Paradise Chocolatier. Located in the heart of Kailua this hub of sweet treats uses fresh fruits, nuts, and spices to craft locally loved chocolates. $$; 20 Kainehe St. sweetparadisechocolate.com or 808/344-1040.
Windward Jewelers. Family owned since 1966, this local gem offers custom, island-inspired jewelry in a range of styles. $$$; 600 Kailua Rd #122; windwardjewelers.com or (808)261-6661.
Global Village. Stock up trendy handbags, flip-flops, and stylish women’s apparel at one of Kailua’s neighborhood boutiques. $$; globalvillagehawaii.com or 808/ 262-8183.