Top 15 Must-Do Activities in Kailua, Hawaii

On Oahu’s eastern, windward side, Kailua is an upscale destination characterized by its dramatic natural scenery and stunning beaches.

Among these, Lanikai Beach exemplifies a tropical paradise, featuring glistening turquoise waters and powdery white sands.

Kailua is geographically separated from Honolulu to the east by the imposing rim of an ancient caldera, ascending 500 meters above the surrounding landscape.

Remnants of this volcano are evident throughout the area, presenting options for challenging hikes with breathtaking views, or engaging in kayaking and paddleboarding amidst sea turtles and monk seals in the crystal-clear waters.

Kailua notably served as the Winter White House during a portion of President Barack Obama’s first term in office.

1. Lanikai Beach

Envision the quintessential Hawaiian beach, and it would closely resemble this expanse of soft, white sand gently lapped by aquamarine waters.

Lanikai Beach consistently ranks among the finest in Hawaii, a fact that is readily apparent upon witnessing its shimmering waters, lush backdrop, and captivating views towards the Mokulua Islands.

As discussed later, kayaking excursions can be initiated from the beach, allowing access to the northernmost of these two islets that accentuate the horizon to the east.

While Lanikai Beach is open to the public, it is not part of any state or municipal park. The shoreline is bordered by a high-end residential area, requiring access via alleyways from designated parking areas.

Recognizing the absence of facilities enhances the beach’s charm; however, it necessitates some preparation should you wish to spend a full day on-site.

2. Kailua Beach Park

Located at the southern end of Kailua Bay, this park is merely a short distance from Lanikai Beach, yet offers all the amenities typically associated with a public beach.

While Kailua Beach Park is second to Lanikai Beach on this list, it would rival any beach across the globe.

Its silky white sands and lagoon-like waters are flanked by a verdant barrier of tall ironwood trees and coconut palms.

Consistent ocean breezes invigorate the area, attracting windsurfing and kite surfing enthusiasts.

For families, the ideal swimming location is situated near the southern end, by the ironwood trees, where a lifeguard station is conveniently located.

3. Lanikai Pillbox Hike

Commencing just behind Lanikai Beach, you can embark on a brief yet highly scenic hike along the Kaiwa Ridge, following the coastline for 1.8 miles.

Around two hours are necessary for a round trip, and while the trail is relatively short, an initial steep ascent is required to access the ridge.

Along the way, hikers will encounter two historic pillboxes from World War II, with the second often being the turnaround point for many.

As with all unpaved trails in Kailua, it is advisable to avoid days following heavy rainfall and to don appropriate footwear.

The Lanikai Pillbox Hike offers stunning scenery throughout, showcasing an expansive view of windward Oahu, including Kailua and Lanikai Beaches, the towering wall of the Koʻolau Range, and the unmistakable Mokulua Islands just off the coast.

4. Kalama Beach Park

A short stroll around the bay from Kailua Beach Park leads to another alluring stretch of white sandy beach, which is somewhat less frequented than its neighboring beach to the southeast.

The tranquil atmosphere at Kalama Beach Park is notable, with upscale residences obscured by a verdant wall of palms, koa, and beach vegetation, and bathers scattered along the shore.

A consistent breeze adorns the area most days, offering ample opportunities to observe kitesurfers and windsurfers in the bay.

The Ulupaʻu Crater lies to the northeast, while the twin Mokulua Islands can be seen to the southeast. For a breathtaking experience, arrive early to witness the sunrise.

5. Paddlesports

A significant aspect of Kailua Bay’s historical prominence stems from its suitability as a landing area for canoes.

Consequently, it is fitting to engage in kayak or canoe rentals on tranquil days, navigating the bay either independently or as part of a guided tour that highlights local wildlife, history, and culture.

Among the marine life, participants may spot monk seals and sea turtles in the clear waters.

The Hawaiian Islands are also recognized as the birthplace of stand-up paddleboarding, making this an ideal locale to try this popular activity.

A selection of watersport companies operates in Kailua, including We Go! Island Canoe, Kailua Beach Adventures, Kailua Ocean Adventures, and Twogood Kayaks Hawaii. Many provide guided tours to the often-visible Mokulua Islands located off the bay’s southern shore.

6. Ho’omaluhia Botanical Garden

This segment of the Honolulu Botanical Gardens, located just ten minutes from Kailua, was established in the early 1980s by the United States Army Corps of Engineers as a flood control measure.

Nestled in the picturesque backdrop of the Koʻolau Range, Ho’omaluhia Botanical Garden serves as a rainforest garden featuring species indigenous to various tropical regions, including those from Sub-Saharan Africa, Malaysia, India, Sri Lanka, Polynesia, Melanesia, the Philippines, and Hawaii.

The diverse flora is organized geographically, creating mesmerizing landscapes against the towering Pali Cliffs. Additionally, visitors can explore the adjacent visitor center and art galleries.

A bird checklist is available for download prior to your visit, and the garden hosts numerous events and activities throughout the year, including camping, catch-and-release fishing, and painting workshops.

7. Mokulua Islands

On particularly calm days, consider arranging for a kayaking or paddleboarding excursion to these two basalt islets located less than a mile off Lanikai Beach.

A variety of local companies, including Kailua Beach Adventures, We Go! Island Canoe, and Twogood Kayaks, offer guided trips to these destinations.

Formed approximately three million years ago, Moku Nui to the north and Moku Iki to the south are both designated as sea bird sanctuaries, with public access granted to only Moku Nui.

Once there, visitors can relax on the pristine sandy beach on the west side, take in views of the Koʻolau Range, leap from cliffs, or snorkel through the abundant lava and coral formations among the sea turtles and crabs.

The islet also serves as an excellent vantage point for spotting humpback whales, typically observed swimming past from December to April.

8. Olomana Three Peaks Trail

Dramatically rising 500 meters above the coastline, this chain of three jagged peaks is a vital feature of the windward Oahu landscape.

Olomana represents a remnant of the Koʻolau caldera, of which the western section prominently marks the horizon toward Honolulu (as detailed further in the subsection on Nu’uanu Pali).

It becomes immediately clear that this hike should not be approached lightly, as it requires considerable scrambling and a fortitude for heights.

Ropes are made available to assist climbers with the steeper ascents, yet some areas necessitate climbing without such aid.

Several incidents of severe injury or fatalities have occurred on the Three Peaks Trail, particularly between the second and third peaks; hence it is advisable to avoid these sections during wet conditions.

The trail spans 4.4 miles but presents the impression of being much longer. Be sure to take a moment to enjoy the remarkable 360-degree views from the first peak.

Many hikers choose to stop here, opting to return rather than tackle the more challenging climbs ahead.

9. Nu’uanu Pali

In just minutes from Kailua, you can traverse the Pali Highway to this breathtaking lookout situated high atop the cliffs of the Koʻolau Range.

From Nuʻuanu Pali, at an elevation of 365 meters, you will enjoy expansive views of Oahu’s windward side, capturing Kailua, the ocean, vast verdant expanses, and the Olomana Peaks.

The wind at this vantage point is quite forceful, often strong enough to support your weight on most days.

This site also bears historical significance; in 1795, Kamehameha I, the founder of the Kingdom of Hawaii, led his troops to push Oahu’s defenders off these cliffs in a campaign aimed at unifying the islands.

10. Ulupō Heiau State Historic Site

A fascinating historical site exists just minutes from downtown Kailua at this significant temple area.

Dating back to the 15th century, the Kailua region was a key center of power for the entire island, thanks to its fertile irrigated fields producing crops like bananas and taro, a rich supply of fish, and safe landing spots for canoes.

Kamehameha I resided in Kailua after his conquest of the island in 1795. The Ulupō Heiau State Historic Site illustrates this importance, characterized by a platform measuring approximately 42 meters by 55 meters, and standing over 9 meters tall.

The stone used in constructing this site was sourced from as far away as Kualoa, roughly 10 miles along the windward coast.

11. Manoa Chocolate Hawaii

As a contributor to the “bean-to-bar” movement, this chocolate maker based in Kailua procures cacao beans directly from growers globally, with an emphasis on local sourcing when feasible.

The origins of the beans, whether sourced from Tanzania, the Dominican Republic, Ecuador, or Oahu itself, are often reflected in the branding of their bars, which generally contain a minimum of 70% cacao.

Noteworthy, location-specific creations from Manoa include flavors such as whiskey, rum, lavender, ghost pepper, goat milk, passion fruit, coconut, and banana.

Visitors can stop by the Kailua factory store for a tour that parallels a visit to a boutique winery or craft brewery.

During your visit, when in season, you may have the opportunity to taste raw cacao fruit and learn about the complete “bean-to-bar” process while enjoying tastings with a knowledgeable “Chocolate Sommelier.”

12. Lanikai Brewing Company

In the same vein, Lanikai Brewing Company crafts beers that hold a distinctive connection to Hawaii and the island of Oahu.

This brewery utilizes local yeast and bacteria and collaborates closely with local farmers, purchasing “ugly” fruits such as pineapple, passion fruit, guava, strawberries, and yuzu.

The brewery’s flagship offerings include Route 70 Saison, featuring a touch of Hawaiian honey; Pillbox Porter, made using rare Hawaiian and Tahitian vanilla; and Moku Imperial, which incorporates pikake flowers for a blend of citrus, tropical, and floral notes.

Lanikai Brewing Company’s brewery and tasting room on Hamakua Drive is open seven days a week and features a rotating draft list that adapts with the seasons.

13. Maunawili Falls

Situated between the Pali Cliffs and Mount Olomana, this family-oriented out and back trail in the Maunawili Valley leads to a breathtaking waterfall concealed within the jungle.

The trailhead is readily identifiable, located in a residential district adjacent to the Royal Hawaiian Golf Club. From this point, hikers will undertake a 2.8-mile trek, navigating over rocks and tree roots, amidst ferns and occasional views of Windward Oahu’s dramatic landscape.

Among the diverse plant species you may encounter are lobelia, ti, mountain apple, ohia, koa, and naupaka.

The falls are positioned just below a picturesque plateau, where the river cascades into a refreshing swimming hole, allowing for jumps into the water from surrounding rocks for the adventurous.

14. Bellows Field Beach Park

Located to the southeast of Kailua at Waimānalo, Bellows Air Field Station is a military reservation that played a pivotal role during World War II.

Although the last runways ceased operation in the 1950s, the station now functions for training and recreational purposes.

This park is accessible to the public on weekends, making the brief trip from Kailua worthwhile for those seeking a peaceful, expansive sandy beach with gentle waves.

A shallow sandbar at this location provides opportunities for body surfing and bodyboarding, and the steady trade winds contribute to a fascinating display of wildlife.

Visitors may spot Portuguese man o’ wars washed ashore (typically occurring 9 to 12 days post full moon), serving as a meal for the small sand bubbler crabs that burrow along the water’s edge.

Overnight camping permits are available through the City and County of Honolulu for those interested in staying longer.

15. Kailua Farmers’ Market

Kailua is home to three farmers’ markets. One operates on Thursday mornings at the Kailua District Park parking lot at 21 South Kainalu Drive.

Another independently-run option is the Lōkahi Kailua Market at 340 Uluniu Street, held on Saturday mornings.

However, the primary market occurs from 4:00 PM to 7:00 PM on Thursdays at the Kailua Town Center Parking Garage, situated at 609 Kailua Road.

Featuring up to 30 vendors, this market is ideal for sourcing seasonal fruits and vegetables, including papayas, Manoa lettuce, bitter melon, breadfruit, guava, bananas, Asian greens, and more.

For locally-inspired delicacies, consider trying ghost pepper salsa, honey harvested from native hives, or traditional Hawaiian specialties like kulolo or haupia.

Furthermore, an array of street food options is available, catering to those craving poke, taro dumplings, Samoan dishes, Vietnamese snacks, noodles, Hawaiian chili, BBQ, or empanadas.