If you don’t already know this about me, lemme fill you in real quick. I try to avoid being a tourist when I travel. Sure, I’ll take LOTS of photos and visit a few famous landmarks (here’s looking at you, Eiffel). But I wanna go beyond that, too—away from the crowds, off the beaten path—in search of adventure and authentic experiences.
Especially in Hawaii. My dad and I spent a week on Oahu back in March, and both had the same mindset: avoid other tourists as much as possible. (Must be where I get it from!) Silly as it sounds, we were proud—yes, proud—that we didn’t step foot on Waikiki Beach. Yeah, yeah. It’s stunning. Iconic. Classic Hawaii. BUT. It’s also a tourist hotbed. Soooo we purposely avoided Waikiki and found some alternatives that honestly gave us a better beach experience, IMO. (Dad’s, too!)
Buuuuuut. More about those beaches in this post. This one’s all about a hike. A real, off the beaten path hike. Oahu has a number of touristy hikes (to use that word loosely) – Diamond Head, Koko Head, Makapu’u Lighthouse – all with brilliant views. And you know I’m all about the views, so we did these hikes. But we also shared the views with at least a dozen other people at any given time. Worthwhile? Yes. But again. I wanted more. I wanted a real, middle of nowhere, authentic Hawaii hike.
That’s pretty much what I told my Airbnb host when he asked about my trip plans. He suggested I follow a few local Instagrammers—friends of his who offer guided tours. So I did. I followed @skoshofyosh (Yoshi) and @full_phil_in_life (Phil). These guys are the real deal when it comes to off-the-grid adventuring in Hawaii. I knew I needed to hang with them, so I booked a hike with Yoshi through their site, Cool Dudes Tours.
Possibly the best decision I made the entire trip.
Friends, I even got to ride in a vintage VW bus! (Not typically part of the experience, FYI). This was Hawaii at its realest. Most real? Nah. I’m gonna stick with realest.
For my hike with Yoshi, I chose the Olomana (Three Peaks) Trail in Kailua. A former Oahu local I know recommended it, so I trusted his judgment. As the name Three Peaks suggests, the full hike requires summiting three separate peaks. Mostly for time’s sake, I only hiked the first two. TBH, I’m not 100% sure I could’ve physically climbed the third (and most challenging) peak—but I surely would’ve tried!
The hike began with a fairly level forest walk. And then it got serious. Killer incline serious, since the first peak is actually the tallest of the three. My lungs and thighs were screaming at me. Every single step demanded caution, confidence, and quick, tactical execution. Once or twice, I even faced the reality of plummeting off the mountain if I lost my footing or grip on the rocks I was climbing. If this sounds dramatic, well, it kinda was. But what’s an adventure without drama?
No question, Three Peaks pushed me beyond my physical comfort zone. More beyond than I’ve ever gone before. But you know what? At no point during the hike did I wish I were doing something else. Not once. I wanted to be there. I wanted to experience the challenge. The fatigue. The uncertainty. The thrill of danger. The confidence to continue. The anticipation of summiting each peak. And the satisfaction that I earned the reward of those 360-degree views. Misty, majestic, and mine.
Looking back at peak one from peak two
But remember. I wasn’t alone. Yoshi patiently lead the way, offering tips and encouragement, and kept me company with some pretty stellar conversation. Honestly, I needed him—his guidance and expertise. Had I attempted the hike alone, per my independent nature, I seriously doubt I would’ve made it to the top of peak #1, let alone #2. Yoshi’s presence gave me the confidence I needed to believe I could do it, and the motivation to keep moving upward (and downward, which was NOT easier).
Yoshi, leading the way up…
Like I said. Booking this hike with Cool Dudes Tours was a smart decision. So smart I’ll do it again the next time I visit Hawaii. After all, I still need to summit that third peak!
For now, though, I’m satisfied with two out of three. Hiking the Olomana Trail both humbled and empowered me. It exposed my weaknesses but made me stronger in the process. Stronger for the next hike. More eager for the next hike. (Switzerland, I’m coming for you!) And that, my friends, is why I will forever seek those real, raw, authentic experiences.
Are you an authentic adventure seeker, too? What’s the most real, raw, authentic adventure you’ve experienced?
*Disclaimer: Olomana Trail is an intermediate to advanced hike, and casualties have increased with its growing popularity. It’s a stunning trek, but a risk nonetheless.