Oahu is ten times more enjoyable by bicycle.

This is Daisaku Kawase, Global Ride’s Communication Director, currently staying on Oahu as the Honolulu Century Ride (HCR) approaches once again this year. Oahu, the host island of the event, offers so much more than just Waikiki — it’s home to many charming and vibrant neighborhoods. If you’ve made it all the way to Hawaii, it would be a shame not to explore beyond the usual spots!

I highly recommend Kailua, located on Oahu’s eastern coast. It’s about 40 kilometers from Waikiki if you follow the scenic coastal route. Kailua is home to the second aid station of the HCR and holds strong ties to former President Obama. It’s also a charming beach town filled with stylish shops. While it might be a bit too far for a Biki share bike, it’s the perfect destination for a one-day ride on a road bike.

The view from the Makapuʻu Lookout

The coastal route is highly recommended for reaching the Kailua area. In fact, the HCR route includes this scenic coastal stretch leading to Kailua, and one of the highlights of the early stages is the breathtaking view from the Makapuʻu Lookout. When I rode the HCR for the first time last year, this was the view that moved me the most. Towering cliffs, the beautifully gradient-colored ocean, and the road winding through the meeting point of these natural wonders—descending that path, I couldn’t help but shout, “This is amazing!”

Kailua is a small town, quite different from Waikiki, with shops and restaurants conveniently clustered within a walkable area.

A favorite spot for locals is ChadLou’s Coffee Roasters, where you can enjoy delicious, freshly roasted coffee. When I asked the staff for a recommendation, they suggested the vanilla-flavored latte. Even iced, the coffee’s aroma and richness shine through—absolutely delightful.

ChadLou’s Coffee Roasters is easily recognizable by its terrace seating.
Each cup was carefully crafted with attention to detail.
They also offer original merchandise like T-shirts and caps.
Vanilla-flavored latte

Along the same row as this coffee shop, you’ll find two of Kailua’s most stylish boutiques: OLIVE and OLIVER.

OLIVE carries everything from clothing to home goods like dishes and cutlery, and it’s all impeccably curated. I picked up a handmade soy candle (28 dollars) with a lovely scent, a lavender eye pillow made with coconut (35 dollars), and palo santo with matches (12 dollars). Hawaii is full of these kinds of feel-good products, and it’s such a delight to find them.

Inside OLIVE store.
The layout is adorable.
The female owner is very friendly and approachable.
The handmade items have stylish packaging as well.

OLIVER primarily carries men’s clothing. From used items to original design T-shirts, everything is effortlessly stylish. I bought one of the original T-shirts.

The owner highly recommended Single Double, the vintage store I mentioned in a previous post. It’s amazing how this sense of style seems to be connected like an underground current.

I heard that the owners of OLIVE are a couple. Both of them have great taste!
Original T-shirt ($48).

For lunch, I recommend Uahi Island Grill. “Uahi” means smoke in Hawaiian. It’s a tidy little diner that specializes in local food. I had the PORK & POKE. You can choose two side dishes, so I picked brown rice and macaroni salad. The slow-cooked pork, kale, and tuna poke were delicious, and the macaroni salad had a mild flavor. The brown rice was cooked soft, and although it looked quite filling at first, I finished it off easily.

An open, well-ventilated restaurant.
PORK & POKE ($22).
Nagai, who accompanied me on the tour.

Located just a minute’s walk from Uahi Island Grill is Mānoa Chocolate & Wine Bar (Manoa Chocolate Factory). This is the famous Manoa Chocolate factory in Hawaii. Here, they generously let you taste their chocolates. Nanase, the staff member, provides an easy-to-understand explanation in Japanese, which is very informative. We sampled about eight different varieties, and each one had its own unique flavor, allowing us to choose the chocolate that best suited our tastes.

The exterior paint is also adorable.
The interior has a counter and is spacious.
Nanaye, who is great at explaining.
The chocolates, carefully selected based on the origin of the cacao, are lined up.

Former President Obama was born and raised in Honolulu. Every year, he would rent a house in Kailua for his vacation, and eventually, he even built a vacation home in this area. Kailua Town offers beautiful beaches and a collection of stylish shops. Buses also run from Waikiki to Kailua. It’s definitely worth stretching your legs and taking a leisurely stroll in this charming town.

Text & Photo＿Daisaku Kawase

🚴‍♂️Related articles🚴‍♂️

Daisaku Kawase’s Bicycle Journey in Hawaii
#01　Honolulu is ten times more enjoyable by bicycle.
#02　Oahu is ten times more enjoyable by bicycle.
#03　For Those Who Want to Enjoy Honolulu Even More.

Honolulu Century Ride 2023 Chronicle
#01　Bike transport: It’s Always a Dilemma (Part 1)
#02　Bike transport: It’s Always a Dilemma (Part 2)
#03　Hawaii was incredibly Hawaii
#04　First Hawaii Ride – Test Run Episode
#05　Ride! Honolulu Century Ride !

Profile

Daisaku Kawase
He is a Free Producer, the Representative of Days Co., Ltd, Global Ride Communication Director.
Born in Aichi Prefecture. With 16 years of road cycling experience, he loves scenic rides. He squeezes in rides between work and travels all over Japan with his bike. His beloved bike is a Trek. After working as a producer on programs like “Ariyoshi no Okane Hakken Totsugeki! Kaneo-kun,” “Oyasumi Japan Nemuiine,” and “Asaichi” at NHK, he became independent in 2022. In addition to producing programs, he also handles project production for government and corporate clients.