By Trip Styler, on October 31, 2013

Country cool in Oahu

Oahu can be overlooked when it comes to Hawaii’s ultimate vacation vision (you + crescent-shaped beach + shade of a rustling palm + rainbow + ukulele). Hawaii lovers hone in on Honolulu, forgetting the rest of the island’s lush landscapes, serene beaches, small towns, and boutique hotels. What’s more, life out yonder is miles away from Honolulu’s humming pace.

On the island’s outer reaches, time is counted in sunrises and sunsets. Nobody takes ‘the small stuff’ too seriously as they stroll through the streets barefoot, or change from a surf or beach session by the roadside. In search of this easy-breezy vibe, a.k.a. my personal state of nirvana, I ventured into Oahu’s corners to tap into its reservoir of cool.


I came to Kailua – a local’s town 30 minutes outside of Honolulu – in search of red velvet pancakes and a beach break. I left with a modern muumuu and shave ice. I was told on ‘aloha’ authority that I could not visit the windward side of the island without having breakfast at Cinnamon’s. When I pressed my fork into the spongy, icing-topped pancake sandwich and reveled in its velvety goodness, I immediately understood the recommendation. My sweet-as-pie server, who called me “honey,” somehow made the dish taste even better.

Hoping to commemorate my island time with a one-of-a-kind souvenir, I strolled over to Muumuu Heaven, a nearby shop that repurposes vintage muumuus (long Hawaiian dress) into modern frocks. How cool is that? Legend has it, the owner wore one of her creations out on the town, and was spotted by fashion icon, Eva Mendez, who bought the entire inventory – on the spot – from the trunk of the seamstress’ car. This story decided my fate: “I’ll take one modern muumuu to-go please.” (I was heading to the beach anyway.)

Island Snow shave ice


One block from Kailua’s calm, crescent-shaped bay known as Kailua Beach, I was lured into a land of frost and flavoring to “test” Obama’s favorite shave ice at Island Snow. In a when-in-Rome moment, I ordered the ultimate shave ice: vanilla ice cream at the base, a snow ball in the center, strawberry-coconut flavoring on top. My shave ice maker suggested I finish it off with a $0.50 drizzle of cream sauce. Done. I was supposed to share it with my sister, but once I tasted it and my eyes fluttered, I abandoned the sharing lessons I learned in preschool, and told her to get her own!

Viewfinder Tip: If you eat shave ice in Oahu – and I suggest you do – always order the optional cream sauce on top. It’s life-changing.

Ko Olina

In Honolulu, my friend and a local told me I had to surf with firefighters. Um, yes; a million times, yes! The session would take place an hour outside Waikiki on the island’s leeward side, so it was a perfect fit for my quest for Oahu’s country cool.


Surfing out to catch a wave

Operating the safest surf school on Oahu, the all-firefighter team at Hawaiian Fire surf school base their lessons on a near-deserted beach in Ko Olina, 10 minutes from the island’s newest resort stretch lined with the likes of Disney’s Aluani. Lance, my instructor and a local fire captain, told me they use foam boards, as well as run lessons faraway from other surfers on beginner-height waves for ultimate safety conditions. Score; safety and a surf session with first responders. For the record, I got up on my third try, and caught every consecutive wave thereafter. Next stop: Banzai Pipeline. Just kidding.

North Shore

I was partially serious when I mentioned the Banzai Pipeline – home to some of the world’s largest waves – on Oahu’s North Shore. Don’t worry, I was going to observe, NOT to partake. The real goal was to spot Kelly Slater, an international surfing sensation and local resident, ride the break. Sadly, I had to settle for the smooth-as-silk beach; no Kelly in sight. (For views like this, I’ll settle any time.)

Banzai Pipeline, North Shore


The North Shore is far from populated, yet strangely, I got stuck in traffic in the midst of my surfing safari. Yep, beach parking procures a spot of traffic on the island’s outer reaches. Once in the clear, I decided to avoid formal beach parking altogether, and do as locals do: park on the roadside, dodge surfboard-toting cyclists, and take a nondescript path to the sandy shore. Here, in my semi-private paradise somewhere between the Pipeline and Sunset Beach I settled in, so immersed in the moment (and the uber-cushy sand), I considered falling backward to make a sand angel.

While I’m not sure if sand angels are a ‘thing’, Oahu’s outer reaches will encourage such behavior. Warning: the cool stuff will bring out your inner nerd. And that’s cool.

Do tell: what are your cool finds on Hawaii’s outer reaches?