Tucked on Oʻahu’s Windward Side, the once-sleepy town of Kailua often charms visitors and locals with its go-with-the-flow vibe and sandy coastlines. Just one look at Kailua Beach and Lanikai, and you’ll be enamored, and you might even be tempted to wake up before dawn to watch the sunrise from the top of Kaʻiwa Ridge.
As you venture beyond its beautiful beaches and scenic hikes, you’ll find a friendly community with cozy coffee shops, trendy boutiques, vibrant farmers markets and plenty of old-school favorites.
Here are just a few reasons to love Kailua, Oʻahu.
1. Kailua Beach and Lanikai
With stretches of gold powdery sand and iconic views of Nā Mokulua, Kailua Beach and Lanikai are the main draws for many on this side of the island.
Photo: Grace Maeda
Spanning 2 miles, Kailua Beach is fronted by clear, typically calm water. While it’s a popular beach, there’s still plenty of space to lounge in peace. Plus, there are lifeguards, restrooms and parking, making it great for families.
Lanikai is not as expansive as nearby Kailua Beach, but it also boasts sparkling waters and an unrivaled view of the two islets off the Windward Coast. The beach is a popular spot to watch the sunrise—and you can easily spend all day here.
2. Kaʻiwa Ridge Trail
One of my favorite places to watch the sun peek above the Pacific is from the top of the Kaʻiwa Ridge Trail, with the Nā Mokulua in the foreground.
Photo: Grace Maeda
Also known as the Lanikai Pillbox Trail, the hike is about 1.5 miles round-trip, with two concrete pillboxes at the summit. From there, hikers have panoramic views of Oʻahu’s Windward Coast.
3. Kalapawai
Photo: Kayla Rivera
Lucky for us, there are two Kalapawai shops in Kailua. The original Kalapawai Market is at the entrance to Kailua Beach. You can pick up coffee, snacks, reef-safe sunscreen and more.
In the heart of Kailua, Kalapawai Café & Deli serves breakfast bagels, hearty sandwiches, loaded burgers, bento plates and pizza.
4. Coffee Shops and Breakfast Spots
With all of the sunrise watchers here, it makes sense that Kailua is dotted with great cafés and breakfast restaurants. If you wake up before dawn and need a black coffee or trendy banana bread latte, you can check out ChadLou’s Coffee Roasters, Morning Brew, Rise and Grind, or The Well.
Photo: Aaron K. Yoshino
For a hearty morning meal, Time’s Coffee Shop has been around for generations, beloved for its banana pancakes, fried rice and hamburger steak. Serving breakfast all day, Over Easy makes breakfast bowls, egg sandwiches, and sweeter options like pancakes and waffles.
5. Please Come Again
Photo: Grace Maeda
One taste of this artisanal ice cream and I knew I’d be back. Please Come Again is a cool ice cream parlor that opened in Kailua at the end of 2024. The shop turns out creative flavors inspired by Hawaiʻi’s cultures, many of them made with ingredients from other local businesses. I love finding chunks of fried pastry from Agnes’ Bakery in a scoop of cinnamon malasada. If it’s not already sold out, try the miso salted caramel: homemade caramel ribbons swirled into a white miso ice cream.
6. Island Snow
Island Snow operates two locations in its hometown. The original is just a short walk from Kailua Beach, perfect for when you need to cool off with a refreshing shave ice. While you can find all of your favorite shave ice syrups here, the business is also known for its clothing line, inspired by Island life.
7. Faria
Photo: Sarah Burchard
At the start of 2025, Kailua welcomed Faria, a comforting space to enjoy home-cooked Portuguese cuisine. Inspired by chef Kawehi Haug’s family recipes and familiar dishes in Hawaiʻi, diners can enjoy Portuguese bean soup, pao doce and more. One of my favorites is the bacalhau a bras, a salted cod topped with slices of boiled egg and olives.
8. Goen Dining + Bar
Goen Dining + Bar has been around since 2018, but I only visited the restaurant for the first time a few months ago. And I’ve already gone back a handful of times. Opened by award-winning chef Roy Yamaguchi, the neighborhood eatery serves an array of shareable plates, including miso eggplant with a delicate texture and beautiful umami flavor and an ʻahi tataki with a mouthwatering spicy ponzu. The sushi rolls are packed with fresh fish and flavor, and you’ll also find favorites like misoyaki butterfish and braised beef short ribs with creamy polenta.
9. The Boardroom
The Boardroom is a tapas bar and lounge, offering spreads like colorful charcuterie, bruschetta with whipped feta and cream cheese, homemade empanadas, fresh carpaccio and paella. Of course, the business mixes libations that pair perfectly with its dishes, from a crisp martini and spicy watermelon margarita to the gin forward butterfly bramble with butterfly pea flower and local honey.
10. Mānoa Chocolate and Wine Bar
You can learn how locally grown cacao is made into gourmet chocolate bars on a factory tour of Mānoa Chocolate. You can also book a guided wine and chocolate experience, where an expert leads you through a tasting of wine and samples of Mānoa Chocolate.
11. Farmers Markets
One of my favorite Sunday morning activities is strolling through the KailuaTown Farmers Market, set up in a parking lot next to Adventist Health Castle. I love picking up bounties of local produce, flower bouquets, kimchi from I Heart Kimchi, vegan macadamia nut cheese from The Vegan Cheese Shoppe and green smoothies from ʻŌmaʻo Man.
Photo: Courtesy of the Hawaiʻi Farm Bureau
On Thursday evenings, the Kailua Farmers Market is held in the parking lot of the Kailua Town Center, organized by the Hawaiʻi Farm Bureau Federation. Alongside booths of fresh produce, you’ll find food trucks and vendors serving empanadas, elote, German-style spaetzle and hand-pulled noodles.
12. BookEnds
I stop at BookEnds about once a week. The charming bookshop opened in the Kailua Shopping Center in 1998. The shelves are lined with new and used books, and every time I return to browse the impressive collection, I notice new additions. The shop also carries reads on Hawaiian history and culture.
13. Twin Islands
As you explore Kailua, you’ll likely notice car stickers and T-shirts bearing the classic design of Twin Islands, a local surf and apparel company.
Twin brothers Mike and Peter Miller grew up in Lanikai and surfed the breaks off Nā Mokulua. After high school, they both surfed professionally. Eventually, they became pilots, like their dad. In 2006, Peter died in a plane crash, and three years later, Mike started Twin Islands in his honor. He designed the logo depicting Nā Mokulua with a wave and an ʻiwa (great frigate bird) flying over, representing Peter. There are two locations in Kailua.
14. Paddling to Nā Mokulua
Nā Mokulua are seabird sanctuaries, surrounded by clear waters and coral reefs. To help protect nesting seabirds, Mokulua Iki, the smaller island, is off-limits to people. But you can kayak to Mokulua Nui, the larger island, and explore the small beach, tide pools and lava formations.
Mokulua Nui is less than a mile off Lanikai, but typically kayakers launch from Kailua Beach Park, making it about 2 to 2.5 miles each way.
Grace Maeda is the editor of HAWAIʻI Magazine.
