We Are Windward O‘ahu: Where Tropical Paradise Meets Suburban Charm

(Sponsored) Windward O’ahu is known for its lush valley neighborhoods and vibrant beach towns. There's lots to do and even more to eat, so people journey from near and far to experience all the community has to offer.

GOOD EATS

From after-beach treats to award-winning meals, the Windward Side offers unique local fare served with a smile and made with aloha.

 Photos: David Croxford and Aaron Yoshino

Prosciutto Rucola – tomato, mozzarella, arugula, prosciutto di parma, pecorino romano.

A favorite Kailua foodie haven is Prima—a modern American restaurant offering kiawe-wood-fired, brick-oven pizzas topped with fresh, local ingredients. Prima owner Kanoe Sandefur had a simple goal going into the restaurant business: to provide good, honest food to the neighborhood he loved. Since Prima’s opening five years ago, the restaurant has blossomed from a small-town eatery into a beloved dining destination featuring creative, award-winning cuisine. Boasting a short, sophisticated menu, Prima offers hearty pasta dishes, fresh fish specials and unique salads—but it’s the one-of-a-kind pizzas that steal the show. Baked in a Stefano Ferrara brick oven, imported from Italy, Prima’s pizzas have the taste of authenticity in every bite. Prima also bring community kids into the kitchen for keiki cooking classes. “We wanted to create a place where kids have the opportunity to be exposed to everything that’s out there, know what goes into the food they eat, and experience the fun behind food,” he says. “Who knows, we may inspire some future pizzaiolo.”

Prima has exciting news for adults, as well. With a newly acquired liquor license, the Kailua restaurant is putting together a fantastic happy-hour menu featuring drink and pūpū specials. 

Housemade Mozzarella marinated in fresh cream served with Vida mixed greens, pear tomatoes and basil.

Ease into the evening with beachside dining and refreshing cocktails at Buzz’s Original Steakhouse. The iconic Lanikai restaurant’s fresh seafood, mouthwatering steaks and smoked meats, and famous pūpū have kept Buzz’s a homegrown favorite since 1962. “We appreciate the business we get from both the locals and visitors that dine with us. We work hard at what we do every day and feel lucky to be situated on a beautiful beach in such a great town,” says director of operations Kaleo Schneider. Even if the parking lot looks busy, Schneider says to pop in anyway—Buzz’s friendly staff will help accommodate you. The family-run restaurant recently received a light remodel, which updated the kitchen facilities and revamped the dining areas while still preserving its historic charm.

Crab and shrimp cocktail with avocado.

New on the menu! Pizza – Creamed Corn & heirloom tomato pizza garnished with fresh Nalo greens.

Lindsey Dymond isn’t just running a restaurant, he’s building a community. As the owner of Kailua’s famous Kalapawai Market and Kalapawai Café & Deli, Dymond understands the importance of connecting with his customers and providing opportunities for future generations. “Kailua is my home—born and raised,” he says. “We strive to be a good neighbor and an active member of our community. We’ve been here for a long time and we want to make sure we’re a part of your day.” The Dymond family’s culture of care and Hale-‘Aina-award-winning cuisine keeps Kalapawai Market bustling and the tables at Kalapawai Café & Deli full. Both Kalapawai establishments offer great selections of sandwiches and burgers—including the house favorite, the Kailua Club—yet each offers services distinct to their respective locations. The Market, a quaint shop steps from Kailua Beach, offers a great selection of healthy, on-the-go meals and snacks. Greeting residents and visitors as they enter Kailua town from the Pali, Kalapawai Café & Deli wows diners with its daily fish specials and classic dishes made from fresh ingredients sourced from local farms. 

New Pau Hana Menu Item! Prosciutto Wrapped Melon – prosciutto, seasonal melon, balsamic honeyglaze, microgreens.

The Dymond family also runs the popular Kāneohe bistro Zia’s Caffe. The after-work and date-night hotspot boasts an upscale menu of Italian comfort food and an extensive wine list. Zia’s early-evening rush inspired its new pau hana menu—with daily discounted drinks, pūpū and dinner items offered from 3 to 6 p.m. “We’re so appreciative of our customers—they make this fun,” says Dymond. Spreading their love of good food westward, the Dymonds are preparing to open a Kalapawai Café in Kapolei this year.

There are several reasons to wait in line for a chance to eat at Cinnamon’s Restaurant—the red-velvet pancakes and the crab-cake eggs Benedict are just two. As a longtime Kailua resident and owner of the hopping breakfast spot, Norman “Puna” Nam, along with his wife, Cricket, and chef Carsie Green, keeps things interesting and tasty with creative menu items. Playful dishes like carrot-cake and guava-chiffon pancakes, macadamia-nut cinnamon rolls, Portuguese-sweet-bread French toast and the signature loco moco are just a few of the culinary creations cooked up by Cinnamon’s innovative chefs. 

Currently testing out a new recipe for liliko‘i chiffon pancakes, perfecting and reinventing breakfast classics is Cinnamon’s specialty. Using fresh, wholesome ingredients, Cinnamon’s offers a satisfying balance of decadence and a healthy kickstart to the day. Longtime residents, newcomers and visitors alike keep the restaurant busy. Nam attributes his restaurant’s popularity and longevity to quality food and his caring staff. “Our staff has made the spirit of aloha and ‘ohana a part of their service and a way of life,” he says. “Our guests can always count on enjoying great food and outstanding service. Seeing the smile of our customers’ faces as they leave and hearing them say, ‘We’ll be back,’ is the best part of my day.”

Bringing a taste of Boston to the sandy sidewalks of Kailua, Bob’s Pizzeria has been serving giant slices of Boston-style pizza for more than a decade. Fresh ingredients, a welcoming atmosphere and consistent quality all keep this quaint Kailua Road eatery a neighborhood favorite. “We try to maintain a strong neighborhood presence,” says owner Robert “Bob” Festa, who donates a portion of his proceeds to various community causes. “We put our hearts into our pizza, and try to provide customers with the best product and value for their money,” he says. The most popular pizzas are the zesty spinach and garlic and the Bob’s Special. Festa emphasizes to his employees that they are part of their visitors’ Hawai‘i experience, and it’s important to help make it an enjoyable one.

COMMUNITY MATTERS

Imagine a place where strangers still wave and smile while passing in the street, and the convenience of a big city exists with a lovely, small-town friendliness. For generations, Windward O‘ahu has grown and attracted community-minded individuals, hoping to share and preserve these special places they call home.

Residents of the Windward Side are able to enjoy state-of-the-art health care resources at a stone’s throw from their front door. Holliday Orthodontics’ team of professionals uses the latest industry technology to provide a comfortable and complete dental experience for their patients. “We wanted to be able to provide orthodontic services to families in Kailua without their having to travel to other areas of the island,” explains Dr. Sean Holliday, DDS, MS, owner of Holliday Orthodontics. “We pride ourselves on treating our patients like friends and family. We believe it is important to have a connection to the community and contribute outside of our work.”

Windward O‘ahu offers a well-rounded education without leaving the local community. One of two K–12 accredited schools in East O‘ahu, Trinity Christian School provides a classical curriculum and extraordinary opportunities to eager learners. Small class sizes, with a cap of 18 students per class for grades PK–6, and 15 students per class in grades 7–12, offer a personalized and attentive learning environment where students thrive. “For us, education is personal,” explains headmaster Stephen Sprague. “We are here to serve our students and their families, and grow together. Our faculty and staff are a wonderful team with a great spirit of unity.” Starting this year, Trinity Christian is expanding its secondary school into two sections and remodeling its campus, adding a sports court and new classrooms, to accommodate an influx of incoming students.

Multi-way Batik Sash skirt worn as dress.

Whether big or small, locally owned businesses thrive on the Windward Side. Noa Noa Hawai‘i brings traditional Native Hawaiian prints to modern fashion with vibrant patterns and dreamy designs. Using the batik method to custom print Noa Noa’s fabric protects the colorful garments from fading. Noa Noa Hawai‘i also offers unique homewares and artifacts from Southeast Asia and the South Pacific—including ninth- to 18th-century Chinese ceramics, ceremonial masks from Indonesia and tapa from all over the Pacific. The Kailua storefront is the newest shop for the local clothing company. “Having a store in a town rather than a mall is interesting and good for developing relationships in the community,” says owner and designer Joan Simon Smoyer. “I live in Kāne‘ohe, so the commute is quite nice.”

Dr. Jeffrey Sonson of Kailua Dental Care agrees that community is everything. Specializing in general and family dentistry, Kailua Dental Care offers a range of services from teeth restoration and cleaning to cosmetic procedures. Along with his business partner, Dr. Ivan Colón, Sonson leads a team of highly trained professionals to offer Windward O‘ahu residents the quality care they need in the convenience of their own community. Kailua Dental Care is focused on preserving the health, strength and functionality of your teeth, and making sure you’re proud of your smile. Providing cleanings and preventive therapy, fillings, crowns and bridges, root-canal therapy, extractions and a variety of cosmetic services—including teeth whitening and Invisalign teeth straightening—the doctors and staff at Kailua Dental Care guarantee exceptional service. “We use the W.I.D.I.O.M. rule, ‘Would I Do It On Mom/Myself?’ and try to treat our patients like family,” says Sonson. The practice also opens itself to patients at extended hours to help accommodate their busy schedules.