A Perfect Day in Kailua

Here is how to best enjoy a day in Oahu’s laid-back suburban beach town of Kailua, with picturesque views of mountains and beaches, a tight-knit community of compact shopping districts, and delicious local eateries.

By Bianca Sewake

Kick-start the day feeling energized with breakfast at Jewel or Juice, a small and colorful shop right outside Kailua Square that offers fresh juices and acai bowls, open every day except Sunday. The Warrior Bowl is a standout on the menu—an acai blend with organic apple juice, topped with fresh and local fruits, bee pollen, honey, and organic granola. Yum. Now it’s time to explore.

Next, take a sunny and breezy drive past Kailua Beach Park and Lanikai homes to the Pillboxes hike (pictured above). The entrance is across from the Mid Pacific Country Club and Golf Course. It’s an easy and open uphill hike that even kids can do, though it begins with a short trek through a clearing of trees on slippery dirt or mud, depending on if there was a recent rain. Before long, the first military bunker—what locals call a pillbox—comes into view. Climb atop for a beautiful view overlooking the homes, sandy beaches, and the Mokulua Islands off in the distance—a popular kayaking spot. The optional second pillbox is further along the path.

By now, it won’t be unusual to see other hikers peeling away clothes down to their swimwear because of the sun’s heat. After reaching the bottom, rub on some sunscreen (if you’re trying to decide which to buy, those with titanium oxide or zinc oxide, which are natural mineral ingredients, have not been found harmful to coral). Zigzag the residential area to find street parking and walk through any path leading to Lanikai Beach, which means “heavenly sea” in Hawaiian. After stepping upon the soft, fine sand and taking a dip in the calm blue waters, it won’t be hard to see how it got its name. Put on snorkel gear to see the little fish swimming around or relax on the beach, watching kayaks pass by.

All that hiking and swimming will work up an appetite. Backtrack to Kailua Square for brunch at Cinnamon’s Restaurant. It’s usually crowded, but don’t shy away. The wait is rarely more than 30 minutes. Ask for indoor seating for a chance to be seated in the little gazebo at the restaurant’s center. While waiting, wander the nearby streets with buzzer in hand to shops like Muse Room. Before long, your buzzer will light up. Try the kalua pork eggs benedict with homemade fries, and share the red velvet or guava chiffon pancakes.

The hearty portions at Cinnamon’s will leave anyone feeling happily stuffed. De-bloat by taking a walk through shops on or near Kailua Road, like men’s surf-inspired boutique Oliver or lady’s boutique Fighting Eel. Peruse the aisles in Bookends, a new and used bookstore with well-stocked shelves and book stacks piled up around the store. The friendly staff can help navigate the way to any specific reads. For a pick-me-up, swing by Morning Brew for an iced cup of joe.

If it’s a Thursday or Sunday, check out the Kailua Farmer’s Market at the Kailua Town Center in front of Long’s and Pier 1 imports. Sample the made-in-Kailua Madre Chocolate, cool down with a homemade popsicle from Ono Pops, or try the Waimanalo Farm’s popular strawberry lemonade or li hing lemonade served in a Mason jar.

After a long day, sit down and relax for dinner at Prima, an Italian restaurant that serves delicious foods while also supporting local farmers. They’re known for their handcrafted kiawe-wood-fired brick oven pizzas. Try the boquerone, a pizza topped with tomato, mozzarella, thyme, onion, garlic, white anchovy, and chili water. Finish off the day’s adventures by unwinding with a drink at Pinky’s Pupu Bar and Grill.