On Oahu’s eastern, windward side, Kailua is an upmarket destination with dramatic natural scenery and beaches of astonishing beauty.
One of these, Lanikai Beach, has all the hallmarks of a tropical paradise, down to the glistening turquoise waters and powdery white sands.
Kailua is separated from Honolulu to the east by the sheer rim of an ancient caldera, climbing 500 metres above the landscape.
There are vestiges of this volcano all around, for some challenging hikes with awe-inspiring views, or you can take to those crystal clear waters, kayaking and paddleboarding among sea turtles and monk seals.
Kailua was the location for the Winter White House for several years during President Barack Obama’s first term.
1. Lanikai Beach
Picture the perfect Hawaiian beach and it would surely come close to this sweep of soft white sand lapped by gently aquamarine waters.
Lanikai Beach is often named among the very best in Hawaii, and it’s easy to understand why when you glimpse the glimmering waters, the lush vegetation behind and the arresting vistas out to the Mokulua Islands.
As we’ll see later, you can embark on a kayak trip from the beach to reach the northernmost of these two islets punctuating the horizon to the east.
Lanikai Beach is public, but not part of a state or municipal park. Buffering the shoreline is a high-end residential neighbourhood, and you’ll get to the beach via alleyways from the parking areas.
There’s also an absence of facilities, which is part of the beach’s appeal, but will entail a little preparation if you want to spend a day here.
2. Kailua Beach Park
At the south end of Kailua Bay, this beach park is a few steps from Lanikai Beach, but comes with all the facilities you would expect from a public beach.
Kailua Beach Park is second to Lanikai Beach on this list but would give any beach in the world a run for its money.
You’ll encounter silky white sands and lagoon-like waters, traced by a green barrier of tall ironwood trees and coconut palms.
As with most of the beaches on the Oahu’s windward coast, the ocean breezes are very consistent, attracting windsurfers and kite-surfers.
For families, the ideal bathing spot is towards the southern end, in front of the ironwood trees, which is where the lifeguard station can be found.
3. Lanikai Pillbox Hike
Starting just behind Lanikai Beach you can embark on a short but very scenic hike along the Kaiwa Ridge, tracing the coastline for 1.8 miles.
You’ll need about two hours for the round trip, and although the trail is short, there’s a stiff initial climb to get up on the ridge.
On the way you’ll come across two historic pillboxes installed during World War II. The second of these is usually the point where walkers turn back.
As with all unpaved walks around Kailua, it’s best to avoid a day with heavy rain and to wear the appropriate footwear.
The joy of the Lanikai Pillbox Hike is the scenery, which is constantly spectacular, encompassing a huge sweep of windward Oahu, including Kailua and Lanikai Beaches, the dominating wall of the Koʻolau Range and the unmistakable Mokulua Islands just offshore.
4. Kalama Beach Park
A short walk around the bay from Kailua Beach Park is another enticing stretch of white sandy beach, a little less frequented than its neighbour to the south-east.
In fact, one of the things that will strike you about Kalama Beach Park is how quiet it is, with only upscale residences hiding behind a wall of palms, koas and beach cabbage, and bathers dispersed around the shore.
There’s a brisk wind most days, and you’re sure to see plenty of kitesurfers and windsurfers in the bay.
Looking out at the ocean you can see the Ulupaʻu Crater to the north-east and the twin Mokulua Islands to the south-east. Try to come early in the day to watch the sun come up.
One of the things that made the Kailua Bay a seat of power centuries ago is its safe landing for canoes.
So there’s something appropriate about hiring a kayak or canoe on a calm day and paddling around the bay, either self-navigated or on a tour to learn about the local wildlife, history and culture.
Monk seals and sea turtles are just a couple of the species you can hope to see in the clear waters.
The Hawaiian Islands are also the birthplace of stand-up paddleboarding, so there’s no better place to try this fast-growing activity.
Just a handful of the watersports companies based in Kailua are We Go! Island Canoe, Kailua Beach Adventures, Kailua Ocean Adventures and Twogood Kayaks Hawaii. Many offer guided trips to Mokulua Islands, ever-present off the south side of the bay.
6. Ho’omaluhia Botanical Garden
This branch of Honolulu Botanical Gardens is little more than ten minutes out of Kailua and was laid out in the early-1980s by the United States Army Corps of Engineers for flood protection.
All the more beautiful in the shadow of the Koʻolau Range, Ho’omaluhia Botanical Garden is a rainforest garden planted with species from tropical regions around the world, among them Sub-Saharan Africa, Malaysia, India and Sri Lanka, Polynesia, Melanesia, the Philippines and Hawaii.
These are grouped geographically and create spellbinding vistas against the soaring Pali Cliffs behind. Also take time to peruse the visitor center and the art galleries next to it.
You can download a bird checklist before your walk, while the garden offers a range of activities year round, like camping, catch-and-release fishing and painting.
7. Mokulua Islands
If you catch a calm day you could look into taking a kayak or paddleboard trip to this pair of basalt islets less than a mile off Lanikai Beach.
There’s a lineup of local companies, like Kailua Beach Adventures, We Go! Island Canoe and Twogood Kayaks, ready to give you a guided trip.
Formed around three million years ago, Moku Nui, to the north, and Moku Iki, are both sea bird sanctuaries, but only the former can be accessed by the public.
Once you get there you can unwind on the pristine sandy beach on the west side, gaze back at the Koʻolau Range, jump from the cliffs or snorkel around the lava and coral formations among the sea turtles and crabs.
The islet is also a good vantage point for spotting the humpbacks that swim past, generally between December and April.
8. Olomana Three Peaks Trail
Rising 500 metres over the coastline, this chain of three jagged peaks is an integral part of the landscape on the windward side of Oahu.
Olomana is a remnant of the Koʻolau caldera, the western section of which dominates the horizon towards Honolulu (see Nu’uanu Pali below).
One look at Olomana and you’ll know that this is a hike not to be taken lightly, requiring a lot of scrambling and a stomach for heights.
Ropes are provided to help you tackle the steeper ascents, but you’ll still need to pick your way up a few walls unaided.
People have died or been seriously injured attempting the Three Peaks Trail, mostly between the second and third peaks, and it’s best to avoid these on particularly wet days.
The trail is 4.4 miles long, but will feel much longer. Be sure to pause at the first peak where you’ll be rewarded with an awesome 360° panorama.
Many hikers come this far and then return without attempting the steeper climbs further on.
9. Nu’uanu Pali
In a matter of minutes from Kailua you can drive the Pali Highway up to this jaw-dropping lookout high on the cliffs of the Koʻolau Range.
From Nuʻuanu Pali, at an elevation of 365 metres, you’ll get a panoramic view of the windward side of Oahu, encompassing Kailua, the ocean, big swathes of greenery and the Olomana Peaks.
The wind up here is formidable, so strong in fact that on most days it will support your weight.
This location also has a violent past, as in 1795, the founder of the Kingdom of Hawaii, Kamehameha I’s troops forced Oahu’s men off these cliffs to their deaths in his campaign to conquer and unite the islands.
10. Ulupō Heiau State Historic Site
There’s an intriguing piece of history a couple of minutes from downtown Kailua at this imposing temple site.
Going back as far as the 15th century, the Kailua area was a base of power for the entire island, thanks to its irrigated fields for crops like banana and taro, abundant supply of pond fish like mullet and safe canoe landings.
Kamehameha I for instance lived in Kailua after conquering the island in 1795. The Ulupō Heiau State Historic Site attests to this importance, with a platform measuring roughly 42 metres by 55 metres, and with a height of more than 9 metres.
The stone for this structure was brought from as far as Kualoa, 10 miles up the windward coast.
11. Manoa Chocolate Hawaii
Part of the “bean-to-bar” movement, this Kailua-based chocolate-maker sources cacao beans directly from growers around the world, as well as from local farms where possible.
The origin of the beans, be it Tanzania, the Dominican Republic, Ecuador, or right here on Oahu, is often reflected in the names of the brand’s bars, most of which have at least 70% cacao content.
Some of Manoa’s location-specific creations include whiskey, rum, lavender, ghost pepper, goat milk, passion fruit, coconut and banana.
You can call in at the factory store in Kailua for a tour, similar to touring a boutique winery or craft brewery.
You’ll get to try raw cacao fruit when in season, will find out everything that the “bean-to-bar” process entails and taste Manoa’s collection in the company of a “Chocolate Sommelier”.
12. Lanikai Brewing Company
In the same spirit, the Lanikai Brewing Company produces craft beer with a special connection to Hawaii and the island of Oahu.
The brewery uses local yeast and bacteria, works hand-in-hand with local farmers, for example, buying up fruit like pineapple, passion fruit, guava, strawberries and yuzu deemed too “ugly” to be sold in stores and markets.
The company’s three year-round flagships are Route 70 Saison, made with a little Hawaiian honey, Pillbox Porter, made from rare Hawaiian and Tahitian vanilla, and Moku Imperial, with pikake flowers contributing to this beer’s citrus, tropical and floral notes.
Lanikai Brewing Company has a brewery and tasting room on Hamakua Drive, open seven days a week and with a draft list that varies with the seasons.
13. Maunawili Falls
Wedged between the Pali Cliffs and Mount Olomana, this family-friendly, out and back trail in the Maunawili Valley will take you to a gorgeous waterfall hiding in the jungle.
The trailhead is easy to find, in a residential area next to the Royal Hawaiian Golf Club. From there you’ll have a 2.8-mile hike, scrambling over rocks and tree roots, with ferns at waist-height and occasional vistas of Windward Oahu’s dramatic terrain.
Some of the plant and tree species you’ll encounter include lobelia, ti, mountain apple, ohia, koa and naupaka.
The falls are just below a scenic plateau, where the river plunges into a paradisiacal swimming hole, and where you can leap into the water from the rocks if you’re feeling brave.
14. Bellows Field Beach Park
On Kailua’s south-east side, at Waimānalo, sits the Bellows Air Field Station, a military reservation that served as a key airfield during World War II.
The last runways were closed in the 1950s, and the station is now used for training and recreation.
The park is open to the public on weekends and warrants the short trip from Kailua if you’d like to relax on a long, wide and soft sandy beach with low-ish waves.
There is a shallow sandbar here for body surfing and bodyboarding breaks, and partly because of the prevailing trade winds there’s a curious array of wildlife.
Portuguese man o’ wars are blown ashore here (9 to 12 days after a full moon), and provide a meal for little sand bubbler crabs, which burrow on the water’s edge.
If you’d like to stay overnight, camping permits are issued by the City and County of Honolulu.
15. Kailua Farmers’ Market
There are actually three farmers’ markets in Kailua. One trades at the parking lot of the Kailua District Park at 21 South Kainalu Drive on Thursday mornings.
There’s also the independently-run Lōkahi Kailua Market at 340 Uluniu Street on Saturday mornings.
But the main event takes place from 16:00 to 19:00 on Thursdays at the Kailua Town Center Parking Garage, 609 Kailua Road.
With up to 30 producers, this is the place to go for seasonal fruit and vegetables, like papaya, Manoa lettuce, bittermelon, breadfruit, guava, bananas, Asian greens and much more.
For delicacies with a connection to the Oahu you could pick up a ghost pepper salsa, honey harvested from local hives or traditional Hawaiian treats like kulolo or haupia.
And there’s a feast of street food on offer, whether you’re hankering for poke, taro dumplings, Samoan specialties, Vietnamese bites, noodles, Hawaiian Chili, Hawaiian-style BBQ or empanadas.