Kailua, located on the windward side of Oahu, is a haven of natural beauty, vibrant culture, and laid-back Hawaiian charm. Whether you're a local looking for new adventures or a tourist seeking the best experiences in paradise, Kailua offers an abundance of attractions that cater to everyone. From pristine beaches and lush hiking trails to charming boutique shops and local eateries, there’s always something to discover. Here’s a guide to the top attractions in Kailua, HI, that will leave you enchanted by this tropical gem.
1. Kailua Beach Park
Kailua Beach consistently ranks as one of the most beautiful beaches in the world, and for good reason. The powdery white sand, crystal-clear turquoise waters, and gentle trade winds make it perfect for swimming, kayaking, paddleboarding, or simply lounging under the Hawaiian sun. Locals and visitors alike cherish this idyllic spot for its relaxed atmosphere and stunning views.
Pro Tip: Rent a kayak or paddleboard and head out to the offshore islands, the Mokulua Islands (affectionately called “The Mokes”), for a truly unique experience.
2. Lanikai Beach
Just down the road from Kailua Beach, you’ll find Lanikai Beach, a smaller and equally stunning destination. With its calm, shallow waters and picturesque surroundings, Lanikai is ideal for families with young children or anyone looking for a serene escape. Sunrises here are legendary, making it a favorite spot for photographers and early risers.
Insider Tip: Parking can be tricky in this residential area, so arrive early or consider biking from Kailua Beach Park.
3. Pillbox Hike (Lanikai Trail)
For those who love breathtaking views and a bit of adventure, the Pillbox Hike (also known as the Ka’iwa Ridge Trail) is a must. This moderate trail rewards hikers with panoramic vistas of Lanikai Beach, Kailua town, and the surrounding mountains. Along the way, you’ll encounter historic World War II-era pillboxes, which add a touch of history to your trek.
Hiking Advice: Wear sturdy shoes and bring water, as parts of the trail can be steep and slippery.
4. Kailua Farmers’ Market
Immerse yourself in the local culture at the Kailua Farmers’ Market, held every Thursday evening. This vibrant market features a delightful array of fresh produce, artisanal products, and mouthwatering local delicacies. It’s the perfect place to sample poke, tropical fruits, and Hawaiian-style baked goods while supporting local vendors.
Don’t Miss: Live music and entertainment often accompany the market, adding to its lively and welcoming atmosphere.
5. Kailua Town
Kailua Town is a shopper’s paradise, blending locally owned boutiques with well-known stores. Wander through charming shops offering handmade jewelry, clothing, and unique gifts. While exploring, stop by one of Kailua’s many cafes or restaurants to savor local flavors like shrimp plates, acai bowls, and Hawaiian coffee.
Local Favorites: Check out BookEnds, a cozy independent bookstore, and the Olive Boutique for chic Hawaiian-inspired fashion.
6. Maunawili Falls
Nature enthusiasts will love the lush, jungle-like Maunawili Falls Trail. This moderately challenging hike leads to a picturesque waterfall where you can take a refreshing dip. The trail winds through dense greenery, offering a true taste of Hawaii’s natural beauty.
Trail Tips: The trail can be muddy after rain, so wear appropriate footwear. It’s also advisable to start early to avoid crowds.
7. Kawai Nui Marsh
For a more off-the-beaten-path adventure, visit Kawai Nui Marsh, Hawaii’s largest wetland and a haven for birdwatchers. This serene area is home to several native Hawaiian bird species and offers tranquil walking paths that highlight the region’s ecological importance.
Educational Opportunity: Learn about the cultural and historical significance of the marsh, which was once an important resource for ancient Hawaiian agriculture.
8. Island Snow
No trip to Kailua is complete without indulging in a refreshing shave ice from Island Snow. This iconic spot is beloved for its fluffy ice and a wide selection of tropical flavors. Customize your shave ice with add-ons like mochi, condensed milk, or ice cream for an extra-special treat.
Fun Fact: Even former President Barack Obama has been spotted enjoying Island Snow during his visits to Kailua.
9. Popoia Island (Flat Island)
If you’re feeling adventurous, take a short paddle to Popoia Island, also known as Flat Island. This small offshore island is a bird sanctuary and offers a unique perspective of Kailua Beach from the water. It’s a great destination for kayaking or stand-up paddleboarding enthusiasts.
Important Reminder: Respect the wildlife and avoid disturbing nesting birds during your visit.
10. Kalapawai Market
Kalapawai Market is a Kailua institution that blends history, community, and great food. This charming green-and-white market has been serving the area since 1932. Before heading to the beach, stop by for a delicious deli sandwich, a cup of coffee, or a picnic supply run.
Pro Tip: The market’s deli menu features fresh and flavorful options, making it a favorite for locals on the go.
11. Mokulua Islands
The Mokulua Islands, accessible by kayak or paddleboard, are an iconic sight off the coast of Lanikai Beach. While the larger of the two islands is open to the public, it’s important to tread lightly as this area is a seabird sanctuary.
What to Bring: Pack plenty of water, reef-safe sunscreen, and sturdy footwear if you plan to explore the island.
12. Kawainui Heritage Trail
Experience a blend of history, culture, and nature along the Kawainui Heritage Trail. This walking trail offers interpretive signs that tell the story of ancient Hawaiian fishponds, cultural practices, and the surrounding ecosystem. It’s a wonderful way to connect with Kailua’s rich history.
A Home in Paradise with Alesia Barnes
Whether you’re visiting Kailua or have already fallen in love with its unique charm, there’s no better place to call home. Imagine waking up to the sound of the ocean, exploring the vibrant community, and enjoying the best of Hawaiian living every day.
If you're considering making Kailua your permanent residence or investing in your own slice of paradise, Alesia Barnes is the Hawaii real estate professional who will guide you every step of the way. With her unparalleled knowledge of the local market and commitment to finding your dream property, Alesia is your trusted partner in the journey to owning a home in Hawaii.
Ready to start your Kailua adventure? Visit alesiabarnes.com to explore listings, learn more about the area, and connect with Alesia Barnes today. Your dream home in paradise awaits!
