Blake Walsh

20 Best Things to Do in Kailua, HI

  • Published 2022/11/22

Planning a trip to Oahu and wanting to explore the best things to do in Kailua?

This census-designated place (CDP) is part of Honolulu County in Hawaii.

Kailua is located in the Koolaupoko District on Oahu’s windward coast.

Kailua is a contraction of Hawaiian words kai (meaning “sea” or “seawater”) and elua (meaning “two”).

One of the best-known Oahu locations for its sandy beaches, Kailua has historical ties to World War II.

Visitors may experience the beach’s natural beauty, sand, and waves in their natural state in Oahu’s less crowded, windy side.

Whether you’re looking for some challenging climbs with breathtaking views or water adventures with sea turtles and monk seals in the crystal blue seas, Kailua has something for you.

Here are the best things to do in Kailua, Hawaii:

Take a Splash at Kailua Beach Park

People at Kailua Beach Park

Osugi /

The popularity of Kailua Beach is easy to understand as soon as you set foot on the shores of the Big Island.

Fine powdery sand covers three miles of crescent beach, which meets beautiful blue seas and blends into the skyline.

In addition, the water stays at a comfortable 75 degrees all year round.

Windsurfing and kitesurfing are particularly well-suited to Kailua Beach’s warm water and offshore trade winds, shielded by a reef.

Sunny day at Kailua Beach Park

E.J.Johnson Photography /

Popular activities include stand-up paddleboarding and kayaking.

Views of the adjacent offshore Moku Iki, Moku Nui, and Flat Islands may be enjoyed from this vantage point.

If the sun is too intense, shade trees, a bike course, picnic tables, facilities and showers, and convenient parking near the beach.

Kailua Beach visitors can park in any three parking lots: one behind Kalapawai Market, another near Kawainui Canal, and a third near Lanikai.

Clean waters and sand of Kailua Beach Park


Grab a Beer by Lanikai Brewing Company

Visit this authentically Hawaiian brewery.

Its creative and savory offerings, all made with locally sourced quality ingredients, are sure to satisfy your thirst for a refreshing beer.

As a result, they buy “ugly” fruits like pineapple and passionfruit from local farmers who don’t want to sell them in stores or marketplaces because they’re “ugly.”

Three of the company’s most popular year-round offerings include Route 70 Saison, Pillbox Porter, and Moku Imperial, brewed with pikake flowers for their citrus, tropical, and floral flavors.

Visit their Kailua tap and barrel tasting room to get a sense of the passion, devotion, and ingenuity of each batch of beer.

They also provide exquisite, made-to-order pizza inspired by the island’s flavors, perfecting their libations.

Go Sunbathing at Lanikai Beach

Scenic sunrise at Lanikai Beach

Shane Myers Photography /

The name “Lanikai” means “heavenly sea,” and with just one look, you’ll see why.

It’s hard not to agree with visitors who say this beach “exemplifies what a day at the beach should be.”

With its tranquil blue seas and perfectly white sand, this beach will make you feel like you’re in a tropical paradise.

As a result, Lanikai is one of the world’s most popular beaches.

Calm waves crashing at Lanikai Beach shore

Phillip B. Espinasse /

It even has a Hawaiian name that translates to “a heavenly ocean.”

As there are no beach signs, it might be challenging to locate Lanikai.

However, there is an entrance to the area marked with “Lanikai” on a pillar.

You may enjoy a wide range of water sports and activities at the beach, great for families with young children and dogs.

Couple sitting on a pillbox at Lanikai Beach

Deborah Kolb /

Go Kiteboarding at Kalama Beach Park

Not far from Kailua Beach Park, Kalama Beach is famed for its white sand and calm surf.

It’s safe to bring kids to Kalama Beach because of the calm surf.

Even those new to surfing or bodyboarding find that the waves here are ideal for learning the sport.

Kalama Beach is less congested than other Oahu beaches, so you can unwind.

Kiteboarding is a favorite pastime for children, and you’ll see a lot of them out and about on the water.

After a long day spent in the heat, you may cool off in the beach’s abundant shade.

Go Hiking through Lanikai Pillboxes Trail

People admiring the view from Lanikai Pillboxes Trail

Gregory Zamell /

Another name for the Lanikai Pillbox Climb is the Ka’iwa Ridge Trail, and both locals and tourists love this hike.

This hike rises above the stunning Lanikai Beach and is considered intermediate.

The first section of the path is the steepest. However, the gradient gradually decreases after that initial stretch.

As you progress, you’ll be rewarded with ever-more-spectacular sights.

Scenic view from Lanikai Pillboxes Trail

MH Anderson Photography /

Two World War I and World War II-era pillboxes (concrete bunkers) may be found on the ridge’s summit as part of Oahu’s coastal defensive network.

Today, they serve as an observation point for the nearby Mokulua Islands, Kailua and Lanikai beaches, and the surrounding neighborhood.

Historically, they were utilized to track water targets and communicate fire coordinates.

You can also view the Waimanalo Bay, Koolau Mountains, Kaneohe Bay, Makapuu Lighthouse, and Mokoli’i Island.

If you’re in a hurry, the trek may be completed in less than an hour, but spare a few minutes to appreciate the stunning scenery.

A person taking photo at Lanikai Pillboxes Trail

Benny Marty /

Learn Standup Paddleboarding with Kailua Beach Adventures

For centuries, Kailua Bay was a place of power because canoes could safely land there.

So renting a canoe or kayak on a tranquil day and cruising around the bay to learn about the local fauna, history, and culture.

Kailua Beach Adventures is a watersports company situated in Kailua.

It also offers Kailua Bay and Lanikai Beach Kayak Rentals, guided kayak tours to Flat Island and the Mokulu Islands, Stand Up Paddle (SUP) Rentals, Snorkel SUP Lessons, and Bike Rentals.

In the crystal-clear seas, you could be lucky enough to encounter sea turtles or monk seals, just to name a few.

Stand-up paddleboarding started in Hawaii, and there’s no better location to get your feet wet in this hot new hobby.

Buy Fresh Produce from Kailua Farmers Market

Kailua’s Enchanted Lake Center’s Enchanted Lake Center parking lot is a popular spot for locals and tourists to shop for fresh produce.

It’s not just a place to buy fresh produce but also a full-blown entertainment experience.

On Sundays, you may mix with the audience and sample delectable cuisine from various vendors at this weekly event.

Those who sit and listen to local musicians perform live can do so at picnic tables and booths.

Freshly cut flowers, locally produced beef, handmade soap and jewelry, fresh eggs, locally crafted vegan chocolate, homemade jam and honey, and much more can be found here in this little town!

Try Andy’s Bueno Salsa’s dill pickle salsa with Ono Pops’ gourmet popsicles.

Climb the Olomana Three Peaks

The tall Olomana Three Peaks

Lostitalianos /

Kailua is dominated by a series of craggy peaks that rise 500 feet above the ocean’s surface.

Nu’uanu Pali may be seen on the horizon towards Honolulu from Olomana, a relic of the Koolau caldera.

When you first see Olomana, you’ll understand why this climb is not for the faint of heart.

It involves a lot of scrambling and will test your nerves of steel.

Aerial view of Olomana Three Peaks

Christian Perry /

The more challenging ascents can be eased by the available ropes, but you’ll still have to scramble up a couple of cliffs on your own.

Most fatalities and significant injuries on the Three Peaks Trail have occurred between the second and third peaks, so stay away from them if it’s raining heavily.

Although the trail is just 4.4 miles in length, it will seem much longer.

At the summit of the first mountain, take a moment to enjoy the stunning 360-degree view that awaits you.

Many hikers make it this far to turn around and head back without tackling the more difficult ascents ahead.

Rainbow over Olomana Three Peaks

Vancamp Popese /

Buy Souvenirs at TikiMaster

TikiMaster is a retailer and wholesaler specializing in Hawaiian art and tikis from all Polynesian Islands.

Among its many offerings are Tiki masks, Tiki sculptures, and more.

Tikimaster was founded in 2000 and has since become one of the most trusted companies in its market for Hawaiiana and Tiki-style items.

In the genuine spirit of Aloha, it provides the most pleasing shopping experience.

Its business owner, Jerome, is always available to assist you.

While it has an online shop, when you’re in Kailua, stop by its 12,000-square-foot warehouse on Kalanianaole Highway and be impressed!

Explore the Wildlife in Kawai Nui Marsh

Calm waters of Kawai Nui Marsh

Nicholas Floyd /

In 2005, this wildlife refuge received recognition for its ecological, cultural, and historical importance.

The Ramsar Wetland of International Importance has been protected in the years afterward.

Awe-inspiring: The most significant wetland in Hawaii covers 830 acres of land.

There are essential roads in the area, including Kailua Road and Kapa’a Quarry Road, which border the marsh.

The sky and clouds reflecting on Kawai Nui Marsh

Nicholas Floyd /

There are four endangered and unique Hawaiian waterbirds that live in this waterbird recovery region.

In addition, the Ko’olau Poko region’s sanctuary serves a vital role in sediment filtering and flood management.

Views of the marsh are possible from several points, even if direct access is limited.

You may get a great view of Kawainui Marsh from the Ulupo Heiau State Historic Site.

The eastern boundary of the marsh may also be viewed from a walking track in Kaha Park.

Lily pads floating on Kawai Nui Marsh

Nicholas Floyd /

Learn More about Hawaiian Culture at Ulupō Heiau State Historic Site

The Ulupō Heiau State Historic Site, now a rebuilt religious site, functioned as a hideaway for lawbreakers and a location to celebrate military victories and plentiful harvests.

A 140-by-180-foot stone platform is the centerpiece of this ancient site.

According to some estimates, it could have been constructed as early as 400 A.D.

One of the island’s most prized natural assets is a 400-acre freshwater pond.

Sugarcane, taro, sweet potatoes, and breadfruit could be grown in abundance because of the islands’ abundant water supply.

Heiau’s base is also home to a lovely water spring.

The Menehune, according to legend, erected Heiau in a single night.

A vast range of herbs, fruits, and vegetables are still grown on the site by residents.

This is a once-in-a-lifetime opportunity for tourists to immerse themselves in Hawaiian culture and history.

Learn How to Make Handcrafted Chocolates at Manoa Chocolate Hawaii

Hawaii-based Manoa Chocolate is a maker of handcrafted, bean-to-bar chocolate.

With an emphasis on dark chocolate, their mission is to create the most incredible chocolate in all of humanity.

Their chocolates are made with affection using fine cacao beans acquired locally.

Visitors are welcome to see their Kailua factory and tasting room.

People may take a 15-minute tour of the plant for $15 each.

It’s a must-see for everyone who wants to get their fill of chocolate.

You’ll also learn a lot about the cocoa business in Hawaii.

A complimentary tasting room is available to visitors.

You’ll get a 10-minute guided tasting tour with sommeliers who are experts in the field of chocolate.

Cacao goods, including cacao tea, unique roasted cacao beans, and chocolate bars, will be available for sampling.

Taste the Local Flavors at Kalapawai Market

Exterior of Kalapawai Market

Kara Knight /

Small-town markets, such as Kalapawai, often became community gathering places, influenced by the people who patronized them.

Its distinctive style has come to represent a more carefree era.

Its menu is flexible enough to meet the dietary needs of each resident.

Hawaii is known for its love of food, and we’ve taken inspiration from the state’s cuisine to create some of our most popular dishes.

Exterior of Kalapawai Market

Robert Linsdell from St. Andrews, Canada, CC BY 2.0, via Wikimedia Commons

As a family-run business, we value each of our employees as an extension of our family.

On a hot day in Kailua, Kalapawai Market is the best spot to have a bite to eat.

Fresh deli sandwiches, coffee, and seafood dinners are available at this establishment.

Those who walk through its doors are immediately struck by its friendly aura.

Meet and Play Board Games with the Locals at Grace In Growlers

This self-serve craft beer pub is 100 percent non-profit.

Grace in Growlers, a Kailua hangout run by Holly and her husband Tim, has grown into a hub for fostering connections within the community.

It’s a great place to meet new people because it has a large community table set up with board games for people to get to know one another.

Grace in Growlers does not provide meals since it encourages guests to bring their own food.

The drinking restriction of 36 ounces helps keep alcohol intake in check and makes this bar a good choice for families.

All of the brews offered at this one-of-a-kind pub come from local brewers that have been carefully vetted.

Go Winetasting at Oeno Winemaking

Kailua is home to the only winery on Oahu.

Oeno Winery creates a diverse selection of wines, including whites, reds, desserts, and Sangria.

The winery tour is a must-do for every visitor to the area, and with good reason.

Learn about the many varieties of grapes and how they are utilized in wine production.

After that, you’ll get the opportunity to taste up to six Oeno wines during an expert-led wine tasting.

Alluring to guests, the warehouse offers a relaxed, laid-back attitude.

They also serve some of the best garlic bread in the neighborhood, so you’ll have something to nibble on as you sip your wine.

Go Shopping and Diving at Aaron’s Dive Shop

Jack Aaron founded Aaron’s Diving Shop in 1971.

It has developed into a prominent dive establishment and is regarded as the island’s top dive operator and diving store.

In the 1980s and 1990s, the owner, Jack Aaron, worked on multiple films, TV shows, and videos as a star trainer and in significant behind-the-scenes capacities.

Swimming, free diving, snorkeling, and spearfishing are some of the skills in which their Dive Shop and Dive personnel are proficient.

They have offered guided and certified scuba dives, diving lessons, equipment rentals, and more for 50 years.

They offer a fully equipped diving store with everything you could need for a day of water sports.

Join a Guided Tour with Sun & Salt Adventures Hawaii

Sun & Salt Adventures wants to allow visitors to responsibly and sustainably explore the special natural world of Kailua, Hawaii.

The guided tour includes a kayak, a safety jacket, paddles, a picnic lunch, and a guide who will teach you how to paddle, lead you securely to offshore islands, and educate you on the birds, aquatic life, and histories of Hawaii while you’re traveling.

This bundle includes a dry bag, cushioned kayak backrest, and snorkeling equipment.

Additionally, there is a good chance of sighting wild turtles or monk seals.

If you’re looking for Kailua Beach kayak rentals or an adventure kayak trip, you’ve come to the perfect spot!

Practice Your Golfing skills at Royal Hawaiian Golf Club

The Royal Hawaiian Golf Club, co-designed by famous designers Peter and Perry Dye, was first played in 1993. Greg Norman, a member of the golfing hall of fame, newly restored the layout.

This course, situated between the gorgeous Mount Olomana and Ko’olau Mountains, is an unforgettable experience with some of Oahu’s most breathtaking sights.

The 45,000-square-foot clubhouse includes everything a player could need, including a par-72 course, locker rooms, and washrooms.

They provide the ideal environment for various events, such as weddings, gatherings, and golf competitions.

Discover one of Hawaii’s hidden secrets by visiting Royal Hawaiian Golf Club immediately!

Rent a Bike at Pedego Kailua and Explore the Neighborhood

After riding one of their chic and incredible electric bicycles for a few seconds or a minute, Pedego Kailua, situated in the heart of Kailua Town, will leave you delighted.

It is one of the top American electric bike retailers, selling a range of models, including cruisers, city, mountain, and fat-tired electric bikes.

They feature a wide selection of extras, colors, and battery options.

Are you annoyed by the traffic on weekends or during holidays? Simply hop on your Pedego and ride about without giving it a second thought.

Take a stroll along the beach, past Kawainui Marsh on the walkway, or just outside Kailua.

Come by today to joyride, rent, or buy your personal Pedego.

Have Breakfast at Cinnamon’s Restaurant

The sole goal of Cinnamon’s Restaurant is client pleasure!

They adhere to the fundamentals of delicious cuisine at fair rates, graciously delivered in a tidy, welcoming, smoke-free environment, and provision wholesome, nutritional meals.

They make an effort to deliver healthy, professionally prepared meals that are well-balanced and devoid of chemicals, preservatives, and additions.

The Baja Breakfast, which includes eggs with green peppers, tomatoes, and cheddar cheese on a crispy corn tortilla with salsa, sour cream, and fries, is one of their unique offerings for breakfast, which is available all day.

Visit Cinnamon’s Restaurant in the center of Kailua town for breakfast or lunch; they also provide catering services.

Final Thoughts

Kailua has everything you’d expect from a Hawaiian town: long, sandy beaches, crystal-clear water, hillside walks, and not a single skyscraper!

It’s just 20 minutes away from Waikiki, yet it’s definitely worth a day trip, if not a place to call home during your vacation on the island of Oahu.

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