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A Nomad’s Guide to Kailua

The ancient Hawaiian chiefs, Ali’i in Hawaiian, used Kailua as the royal playground of Oahu. In modern times the sentiment has not changed. The sleepy surf town has been an oasis for Hollywood stars, US Presidents, tycoons and business elites.

The lush tropical backdrop of the Koolau Mountains melded with the crystal blue mellody of Kailua Bay forms a symphony of natural beauty and free-spirited lifestyle. This aesthetic makes Kailua a popular destination place for the wayward explorer.

Kailua is an ever changing tapestry. Home to the Marine Corps Base Hawaii, one of the highest density of transplants on Oahu, and popular destination place for tourists, Kailua has an eclectic mix of people from all around the world.

Nevertheless, despite Kailua’s international popularity, it does not cater to tourist like a designated tourist district like Waikiki. Here is a quick guide to Kailua for the nomad



Kailua is home to one of the most beautiful coastlines in the world. Kailua Bay’s coastline is a mosaic of a military base, seaside hills, and high-end beachfront homes. Despite most of the beaches being tucked away from public view, they are all publically accessible.

Kailua Beach

Kailua beach is the most accessible of those on Kailua Bay. It is in skipping distance to Kailua Town and offers the excellent convenience store, Kalapawai, and magnificent restaurant, Buzz’s Steakhouse, adjacent to the beach.There is usually an eclectic mixture of international tourists, and the beach is like a scaled down Waikiki.

Lanikai Beach

Lanikai beach is tucked away in Lanikai crater, which is a hidden grotto of luxury homes owned by billionaires and movie stars. Often considered one of the nicest beaches in the world it is very popular amongst the locals and tourists. It contains the classic backdrop of the Mokulua Islands, which is an iconic symbol of Kailua. However, keep in mind that parking can be tough. Thus, pro tip: ride a bike

Kalama Beach

Kalama beach is a little off the beaten path. This beach has gained a lot of popularity over the years, outside of the local community, and is a good alternative for those who are looking for a less touristy vibe.


There are few pristine hikes in Kailua ranging from beginner to expert. Most will accesend you to picturesque heights and/or with beautiful backdrops. Here are a few -- but not all -- of them listed from extremely easy to death defying.

Marsh Dike Trail

The Marsh Dike Trail is a casual stroll through the backside of Kailua which offers and amazing view of Kawainui Marsh and the Koolau mountains. It is not often utilized by tourists, surprisingly, yet the locals utilize it frequently as it offers a spectacular view of the mountains and is a simple one-way 1.3 mile walk or bike ride.


The Lanikai Pillboxes is a must do hike for both the casual and hardcore hiker alike. It is icon Windward hike. It is short and moderately intense, but it offer a spectacular view of the Mokulua Islands, Lanikai Beach, and gorgeous 360 degree view of Kailua and its neighboring districts.

Olomana Three Peaks Trail

The Olomana Trail is a pristine tropical rainforest hike that can be done by anyone up the first peak or down to the pond. However, do not venture past the first peak unless the conditions are good and you are an expert hiker and rock climber. The trail can be treacherous and even experienced hikers have died taking up the challenge. Do not push your limits on this hike.


Kailua has a reputation for great restaurants -- especially its breakfast spots. There are a ethnic mix of hole-in-the-walls, upscale eateries, and commercial franchises. Here are some recommendations for breakfast, lunch, and dinner.



Cinnamon is mainstay in the Kailua’s Breakfast scene. It is a Hawaii-style dinner famous for its assortment of delicious pancakes. It has a nice outdoor courtyard, relaxing interior to eat, and a well priced menu. Its staff is very friendly and hospitable. However, Cinnamons is often busy and there are long wait time if you go during peak hours on the weekends. So either go before 9 am or after 11:30 am if you don’t want to wait in line.


Moke’s is another Hawaiian style dinner. My recommendation would be the Prime Rib Loco Moco, a twist on traditional local breakfast dish. There is also a wait time if you go during busy hour, but it is well worth the wait if you want a hearty breakfast dish.

Crepes No Kai Oi

Crepes No Kai Oi is a laid back place to grab an simple breakfast. My recommendation would be the Ultimate Breakfast Crepe which is a savory crepe filled with eggs, bacon, potatoes, and cheese, and come with a side of Hollandaise sauce. yumz.


Whole Foods

Whole Foods has a good assortment of food, and not as expensive as you’d think. My recommendation would be the smoked food section in the back. However, there is a social bar and restaurant with indoor and patio seating.


Hibachi is not technically a restaurant but a little liquor store at the edge of Kailua. However, they have a prepped meat section in which you can have them grill up a dish for you and eat it on their tables outside. My recommendation is the lamb.

Down to Earth

Down to Earth is a health food grocery store at the border of Kailua. It has a good vegetarian buffet. I recommend the potatoes au gratin.



If you are in the mood for good Japanese food Tokonami is the best spot in Kailua. There is a quaint atmosphere and an amazing sushi bar. My recommendation would be the furikake salmon and finish it off with the green tea ice cream for dessert.


Prima is a modern pizza restaurant with new twist. The walls are covered with retro paintings and they play an eclectic assortment of music. My favorite is the prosciutto and arugula pizza and the beef bone marrow.

Willow Tree

Disney got it wrong when they said that they are the happiest place on earth: it’s the Willow Tree. The food from this family ran restaurant heals my soul. It somewhat falls in the hole-in-the wall with amazing food category. My recommendation is the Kalbi dinner, but quite frankly I could throw a dart at the menu and be happy with whatever it lands.



ChadLous is hands down my favorite coffee shop in Kailua...maybe the’s definitely one of my happy places. There I fuel myself with americanos and stuff myself frittatas. Its low-key location makes for an laid back spot off the beaten path.


Kalapawai has great food and coffee all around. They have tasty sliders for breakfast and amazing double-cut pork chops for dinner.


The Beer-muda Triangle of Kailua

The longstanding bars in Kailua are Boardrider’s, Creekside, and Bob’s. I call these the Beer-muda Triangle of Kailua because people often migrate between the three throughout the night. They are definitely your a-typical watering holes, but a lot of fun nevertheless.

The Pub

The Pub is popular amongst the military crowd. It’s a good place to watch a game during the afternoon. It’s a bit small and smelly, but fun nevertheless. There grill is pretty good if want bite to eat.

Tap and Barrel

Tap and Barrel is the new kid on the block when it comes to Kailua bars. It is technically in the Beer-muda Triangle, but it fall into the artisan category for me, as they sell craft beer, with interesting flavors. Tap and Barrel is definitely worth a gander if you’re looking to change it up.

In Conclusion

This guide is a brief overview and jumping off point of what Kailua has to offer. Of course, exploration is always the most satisfying, so go out there and get off the beaten path and find what is suitable for what you enjoy most.

Kailua is an ever changing tapestry of businesses and community. Its hidden gems are always changing and I’m discovering something new about it all the time. So if you find something awesome that we missed please let us know in the comments!

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