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The Top 10 Reasons to Love Kailua

Kailua is a special place. This beach town on the Windward side of Oahu was largely unknown 15 years ago, but the secret’s out now. Lanikai Beach, the Pillbox hike, President Obama’s family vacations while he was in office, the list of reasons Kailua is on the map go on and on. Spend an hour here and you’ll notice there’s something different. It’s not just one thing, it’s a number of tangible elements that create the intangible quality that’s unique to Kailua. Here, we’ve laid out the top 10 things that set Kailua apart.


Kailua Beach Park - Aerial Photo

Kailua Beach Park

Kailua is home to some seriously beautiful beaches. Kailua Beach and Lanikai feature fine white sand, clear blue water, and amazing views in every direction. Kailua Beach stretches about 1.5 miles along Kailua Bay. Kailua Beach Park has 2 entrances and is outfitted with parking areas, restrooms, showers, and lifeguards on duty. Kayakers head into Kailua Bay here, as do surfers, paddleboarders, and kite surfers. There’s a swimming area marked by buoys where boats and boards are restricted, and plenty of fun to be had in the shore break up and down the beach.

Lanikai Beach

Lanikai Beach

Lanikai is a smaller stretch of beach just south of Kailua Beach Park. The water is calm year round, so it’s a great place for children, and the water is exceptionally crystal clear. Lanikai is great for swimming, snorkeling, or setting up an umbrella, cooler and spending day. Look out at the Mokulua Islands straight in front of you or the Koolau Mountains stretching in either direction behind you. Lanikai is a residential neighborhood; a one way road is the only way in and out. There are no showers, restrooms, parking lots or lifeguards. Parking is on the street and can be especially hard to find on the weekends. Biking or walking can save time and headaches. Once you make it to the beach though, you’ll understand why it’s so popular.

With such beautiful beaches, it’s no surprise that getting in the water is part of the Kailua lifestyle. There’s literally something for everyone, no matter your age or level of fitness. This part of the island is called the Windward Side for a reason. Kailua Bay is known around the world by kitesurfers because of the tradewinds that blow year round. The lack of shallow reefs makes the bay a safe place to learn and, when the winds are really blowing, the more experienced kiters come out in force. For traditional surfers, there are a number of breaks off of Kailua and Lanikai. On calmer days, taking a kayak or stand up paddleboard (SUP) out to Flat Island or the Mokulua Islands is a popular activity. You can rent boards, kayaks and take lessons at shops including Hawaiian Watersports, Kailua Beach Adventures and Kimo’s Surf Hut.

Canoeing at Kailua Beach Park

Canoeing at Kailua Beach Park

Outrigger Paddling is also a highly competitive sport in Kailua. The Lanikai and Kalua Canoe Clubs have teams for every age, from young kids to seniors, at novice to advanced levels. Be warned though: joining a team is not a minor side activity, it’s intense and competitive, but it’s a great way to meet people and both clubsi are among the top teams in the state year after year.

Shopping Local

Lanikai Bath & Body Shop

Lanikai Bath & Body

Kailua is full of locally owned boutiques offering art, clothing, lotions, beauty products, jewelry and gift items that are island-inspired and made in Hawaii, some made right here in Kailua! Fighting Eel, Noa Noa, Global Village, Lanikai Bath & Body, Kailua General Store, Island Treasures Art Gallery and Windward Jewelers are just some of the shops you can explore if you want something with a local touch.

Kailua General Store

Farmers Markets

Kailua Thursday 5pm to 7:30pm Farmers Market

Thursday 5pm to 7.30pm Farmers Market

Speaking of shopping local, Kailua’s 3 weekly farmers markets give residents and visitors a chance to buy produce from local farms, support vendors selling things like local honey, kombucha, salsa, jellies, juices and cheese, and enjoy a variety of ready to eat food including burgers, crepes, waffles, sushi, and vegan dishes.

The farmers markets are put on by different and organizations and each offers something different.
Thursday: 9:00am – noon, Kailua Recreation Center parking lot
Thursday: 5:00 – 7:30pm, Long’s Drugs parking lot
Sunday: 9:00am-noon, Kailua Elementary School
The Thursday evening and Sunday morning markets are the busiest, offer the most selection, as well as entertainment. They are popular community events and should be experienced at least once!


Sunrise in Kailua - Seen From Lanikai Beach

Sunrise in Kailua

Each morning the sun rises over Kailua Bay and, while it’s always different, it’s always spectacular. If you’re lucky enough to have a home fronting the beach, you can enjoy the sunrise every morning from the privacy of your home. If not, take an early morning walk or run on the beach, hike up to the Pillboxes, or paddle out on a kayak, surfboard or SUP. The natural beauty will energize and inspire your morning!

Beach Living

Lanikai Homes - Aerial Photo

Lanikai Homes

Kailua real estate includes some very desirable neighborhoods, including luxury Lanikai and Kailua Beachside. In a sense, Lanikai is it’s own beach community within Kalua. Beautiful, island style homes line the beach and the hillside on the inland side of the loop. Residents are friendly and get to know their neighbors; there are not many private, gated homes here. It’s also an active community, where you’ll see people running, walking, and biking the loop from sunup to sundown, paddling out on surfboards, SUPs, kayaks and outrigger canoes, or heading to the pillbox trail. It’s also home to Mid Pacific Country Club, which has a beautiful golf course, fitness center and other amenities.

Kailua Beachside Homes

Kailua Beachside

Kailua Beachside homes feel a bit more private and exclusive than homes in Lanikai. There are a number of lanes and loops off of N. Kalaheo Drive, so significantly fewer people walk, bike or drive past these homes. Residents are friendly, but each street feels like its own small neighborhood. Because Kailua Beach is larger than Lanikai, it’s much less crowded. This is a better choice for anyone looking for a quieter, more private area.

Maunawili Homes on Kika Street


Other neighborhoods in Kailua offer homes that don’t come with the beachfront price tag. Maunawili, at the base of the Pali Highway has beautiful homes in what feels like a rainforest. It’s at the base of the Koolau Mountains, quiet and very peaceful. It’s about a mile outside of Kailua Town, which can be a positive or negative depending on what you’re looking for. The Enchanted Lake neighborhood, along Keolu Drive, is a popular family area filled with parks, an elementary school, and a shopping center. Many Enchanted Lake homes enjoy access to canals that lead to Kailua Bay. There are also a variety of condo complexes on Aoloa Street in Kailua Town. From high rise Windward Passage, to the more exclusive Windward Cove and Windward Harbor, to the treehouse-inspired Gardenia Manor, these condos can be great options for first time buyers, for singles, young couples, or parents whose children have “left the nest.”

Healthy Living is a Way of Life

Makai Bowls Kailua

Makai Bowls – Serves Excellent Acai Bowls

Kailua is home to people who are active, conscious about what they eat, where their food comes from, and put importance on the mind, body and soul. Stay fit at a variety of boutique gyms, yoga and pilates studios, or head outside to walk, run, hike, bike or get in the water. Find healthy food options at local spots offering fresh juices, smoothies and acai bowls, made to order salads, sandwiches and plates, or sit down for dinner at a number of restaurants using locally sourced ingredients in their menus.

Walk & Bike Everywhere
Kailua is incredibly pedestrian friendly. It’s one of the only places on island where you can bike or walk all over town. There are bike lanes, bike paths, and sidewalks from the Pali Highway into Lanikai. With Kailua’s increased popularity, traffic has increased as well, so in many cases, it’s quicker to bike to run errands or go to the beach, especially when you consider the time it can take to find parkingl. There are bike racks to lock your bike at every shopping center, places like Pedego and The Bike Shop, where you can rent a bike for the day, and pedestrian friendly crosswalks all over town.

Driving over the Pali.

View from Pali Lookout

Pali Lookout

Unless you work from home, work in Kailua, or are enjoying retirement, most Kailua residents head to Honolulu or elsewhere on the island for work. The Pali Highway runs straight into Kailua from downtown Honolulu, cutting through the Koolau Mountains and offering stunning views. Head out of Honolulu, make it through the tunnels, and you’re rewarded with a panoramic view of the lush mountains, Kaneohe, Kailua and their respective bays. If it’s rained, you’re likely to see waterfalls on your drive, and there are impressive views from the Pali Lookout and scenic viewpoints on the Kailua side of the tunnels where you can stop and take it all in. Even if there’s traffic, many residents say that they start to breathe easier because they’ve left Town behind them. (The H3, connecting the Windward Side to Central Oahu, is also a beautiful drive with impressive views of the mountains and Windward Oahu.)

Holiday Celebrations
Kailua’s small town feel is enhanced by events and celebrations that bring everyone together. On July 4th, an annual parade continues a decades-long tradition. Residents line the streets to enjoy the procession and cheer.. That evening, residents head to the beach, to the pillboxes, or to their rooftops if they’re lucky, to watch the annual fireworks show. This community funded extravaganza brings friends, family, and visitors together every year.
The annual Christmas tree lighting at Castle Hospital is another Kailua event that gets island-wide attention. At the beginning of December, residents gather to enjoy music, sing carols, and watch as the lights at Castle Hospital are turned on. The lighting brings the town together and is a great kick off t o the holiday season.

With about 15,000 homes and over 50,000 residents, Kailua is not exactly a small town. However, it’s managed to keep that small town feeling. Everything you need is here, from grocery stores, to shopping to home services to great restaurants. Unless you want to leave, you really don’t have to. With so many events, activities, and things to do, it’s easy to meet people and feel like you’re part of the community. It’s truly a beautiful place and residents take pride in maintaining that beauty. But the heart of the community is something you just don’t find everywhere. We’re not sure if the place makes the people or the people make the place, but we do know that Kailua has a very good thing going on!

The Top 10 Reasons to Love Kailua was last modified: September 6th, 2021 by Hawaii Living

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