Take a trip to the Windward side and discover some of the best things to do in Kailua Town. You’re in for a treat as you'll be surrounded by incredible delicious restaurants, cute boutique shops, a couple neat breweries, and even a chocolate factory where you can take a tour and sample some high end Hawaii made chocolate. And if you can make it 5 minutes past the glory of this town, you will also discover a couple of the most beautiful beaches on Oahu, including Kailua Beach and Lanikai Beach.
Once a sleepy neighborhood with not much happening on the Windward side of Oahu, is now full of lots of things to do in Kailua.
Over the past decade this pleasant quaint town has been experiencing a renascence of new shops and restaurants.
But it’s the outdoor activities and easiness of getting around that’s driving tourist over the Pali Highway and spending more time here.
And unlike the north shore that takes a good hour to get to, you can arrive in Kailua Town from Waikiki in under a half hour.
Whether you decide to climb to the peak of the Lanikai Pillbox Hike for a spectacular view, go for a morning swim in aqua blue waters at Kailua Beach, kayak to the Mokulua Island, rent a bike and ride along the coast, or spend a lazy afternoon in town enjoying a shave ice and looking for a perfect souvenir, Kailua has something for offer everyone.
Most visitors pass right through the 3 square block town to get to the beautiful beaches, but it is worth pulling over and exploring.
Peruse the Hawaiian book collection at Bookends, check out the poke bar in Whole Foods, and sample different types of chocolate from a local chocolatier called Mano.
Also admire local art creations at the Island Treasures Art Gallery, and grab yourself a shave ice from Island Snow as you head off to the beach.
You could also rent a bike in town to ride around and check out the surrounding area including the beaches. There are a few places that provide bike rentals including Kailua Bicycle, The Bike Shop, Pedego Electric Bikes, and Kailua Beach Adventures. They are easy to rent and start around $20
Parking along Kailua Road will give you access to a good sample of fun boutique shops to explore. And while you will discover most by simply walking around and exploring, here are a few we would like to highlight…
One of the last few bookshops on Oahu, and the only one in Kailua Town. You’ll see aisles and stacks of books as you would in most shops, but it’s the extensive Hawaiiana Book section that most visitors are interested in at BookEnds.
Old Hawaiian history, Colorful Island Photography, Arts & Crafts, Folk Tales, Pidgen English Joke Books, and lot more to be found in this section.
600 Kailua Rd #126, Kailua - (808) 261-1996
Open daily from 9 AM to 8 PM, except closes at 5 PM on Sunday
This cute shop features lots of neat creations by local artist. You’re bound to fall in love with something where its handmade jewelry with seashells, island printed hats, pineapple salt & pepper shakers, owner designed shirts, and everything in-between.
539 Kailua Rd #104, Kailua - (808) 262-8183
Open daily from 9:30 AM to 6:30 PM, except Sunday 10 AM to 5 PM
Step into the beach scene before you walk on any sand! Lots of beach signs, seashell printed home décor, and coastal natural colored jugs, baskets and other items for sale. It a good feel shop to step into even if you plan on buying nothing.
539 Kailua Rd #106, Kailua - (808) 772-4805
Open Mon - Thurs 9 AM to 7 PM & Fri - Sun 9 AM to 8 PM
Another must see Hawaiiana galore shop on this side of the island. Red Bamboo is an eclectic store filled with lots of artist paintings hanging on the walls, personal creations including picture frames, candles, and shell chandeliers. They even feature year-round local Christmas items to take home for the holidays.
602 Kailua Rd #101, Kailua - (808) 263-3174
Open daily 9:30 AM to 6 PM
For many years Buzz’s Steakhouse that’s located across the street from Kailua Beach was about the only memorable place in town for its location and long standing run.
When I think of Kailua Restaurants today, brunch spots come to mind as they have some of the best! Boots & Kimo’s, Cinnamons, Moke’s Bread and Breakfast, and Over Easy and all excellent choices with delicious spins on pancakes, fried rice and loco mocos…you will not be disappointed!
Keep it simple, filling, and onolicious (delicious) by grabbing a plate lunch in town. If you’re not familiar, this is local comfort foods that are well regarded in Hawaii.
Kailua has its share of classic plate lunch spots including L&L Barbeque, Zippy’s, Kim Chee Restaurant, Koko’s, and Fatboy’s Kailua Town. There nothing more stratifying than picking up some Hawaiian comfort food barbecue and taking it to the beach for a picnic.
We personally like the Ohana Bar-B-Q for the quality and generous portions. A mixed plate lunch here can feed the whole family!
Recently a couple breweries have popped up in town. Stop by the Lanikai Brewing Company for tastings of their Moku Imperial IPA, Pillbox Porter, and Hawaiian Wild Ales, and learn about their brewing process.
The Maui Brewing Company has also opened up in town with a restaurant & bar tied to it. The wall murals, hip island décor, and outdoor seating makes it one of the coolest places to hangout for happy hour.
Aqua blue waters, long powdery sandy beaches, calmer waters, trade winds and sunshine are what make up these beautiful Oahu beaches! The question is do you want to go to Kailua Beach, neighboring Lanikai Beach, or Kalama Beach located down the road? There are no bad choices here, but learn more about them and how they differ from one another.
This Oahu beach is just a couple minutes past town. It has lots of public parking, restrooms, a large grassy field with picnic tables, and trees providing some shade.
Kailua Beach Park is also has an extensive beautiful beach with playful water to jump into.
Voted as Oahu’s #1 most beautiful beach, tends to be a little overrun because of its popularity.
If you manage to find a parking spot in the Lanikai Beach residential neighborhood, and walk through one of the 3 beach alleyways, you’ll see why this was named “Heavenly Water”.
Located on the opposite side of North Kalaheo Ave is Kalama Beach Park. It tends to be quitter on this side and a locals favorite. There not much public parking available, but there’s no shortage of pristine beach here…goes on for miles!
Like renting bikes in town, you can also rent kayaks in town or sign up for tours that make it easy to participate in this water sport.
Whether you decide to stick close to coast and admire the beaches and homes or make the journey out to the Mokalua Islands and back, I'm sure you'll have fun!
There are guided kayak tours available with gear provided...
known for its short climb up to a couple military viewing pillboxs, with some of the most stunning views of Mokulua Islands, and the vast majestic blue waters surrounding the Windward side.
The Lanikai Pillbox Hike is an adventurous mile hike with rewarding views.
known for its short climb up to a couple military viewing pillboxes, with some of the most stunning views of Mokulua Islands, and the vast majestic blue waters surrounding the Windward side.
Start off from Waikiki, and travel on the number 20 bus up to the Aloha Tower bus stop. Take a paper transfer and jump onto bus number 57 to the downtown Kailua Town area.