Our Hawaii Story

I had no way of knowing it at the time, but stepping off that plane in Maui would alter the course of my life. Hawaii wasn’t just another place to visit; it felt like coming home. I was mesmerized by the islands’ raw beauty, from the verdant valleys along the Hana Highway to the expansive misty summit of Haleakalā. The land, culture, food, the spirit of aloha — it all left an imprint on my soul. I knew I had to share it with the world.

In the fall of 2002, with a passion for travel and an emerging skill in web development, I launched my first Hawaii-focused website: MauiGuide.net. It started as a personal project, an expansion of the Maui-focused photo journal website I had previously launched immediately after my trip (similar to what I had done for Alaska). Ultimately, the early website was a simple way to document my experiences and offer advice to fellow Maui travelers. But it didn’t take long for me to realize that there was a real need for accurate, independent travel information about not just Maui but all of Hawaii. The mainstream guidebooks and visitor guides felt impersonal; their advice was often tailored more for advertisers than actual visitors. I wanted to create something different: a guide written by someone who truly loved and understood Hawaii. I wanted to provide it for free and I wanted to build it online.

As interest in the site grew, so did my ambition. Over the next few months, I expanded beyond Maui, building guides for Kauai, the Big Island, and Oahu.

By the spring of 2003, I had consolidated everything under Hawaii-Guide.com, creating a one-stop resource for travelers looking for honest, experience-driven insights on where to go, what to do, and how to experience Hawaii responsibly.

A couple of trips later, as the idea took root, in 2005, I officially incorporated the business in my home state as the 'Hawaiian Style Organization.'

Taking the Leap: Turning a Passion into a Full-Time Career

For years, I balanced my growing business with a full-time job in the public & private sectors. It wasn’t always easy—early mornings, late nights, and weekends spent refining the site and writing new content. If I took time off from work, I was in Hawaii - working on HawaiiGuide (I realize I could have picked a worse 'side hustle'). Deep down, I knew where my heart was. I wanted to commit fully to the business, to give it the time and energy it deserved. 

In 2014, after 12 years of working on the business as a side project, I finally made the leap, leaving my job as VP of Operations for a local web firm behind to focus entirely on Hawaii Guide. It was both exhilarating and terrifying—walking away from the stability of a traditional career to embrace the uncertainty of entrepreneurship. But it was the right decision. It took time, patience, and a lot of hard work, but the business flourished, and with it, my connection to Hawaii grew even stronger.

A Partnership in Business and Life

Hawaii didn’t just change my career—it also changed my life in a much deeper way. In 2011, I married my wife, Victoria, on the island of Kauai. It was a fitting place to say “I do,” as Hawaii had already played such a pivotal role in my journey. Standing together beneath the towering peaks of Hanalei, we knew this place would forever be a part of our story.

In 2016, Victoria officially joined Hawaii Guide, bringing her expertise in writing, publishing, and business development. With her passion for travel and storytelling, she helped elevate the company, expanding our reach and refining the experience for travelers. What started as my personal project had now become a true family business, built on a shared love for Hawaii and a commitment to helping others experience its magic.

Looking Ahead: Honoring the Past, Embracing the Future

Of course, the journey hasn’t always been smooth. Building and maintaining an independent travel website—especially one competing with big-name and well-funded entities has had its challenges. Algorithm changes, economic shifts, global pandemics(!!), and industry disruptions have tested our resilience more times than we can count. But if Hawaii has taught us anything, it’s that persistence is key. Like the ancient lava flows that shaped these islands, progress takes time and patience.

Through it all, our love for Hawaii has remained unwavering. Over the past two decades, HawaiiGuide has grown into the largest independent travel site dedicated to the islands, second only to the state’s official tourism website. Along the way, we’ve deepened our connection to Hawaii, learning from locals, respecting the land, and striving to promote responsible tourism that honors the islands’ unique culture and ecosystems. Here's how we earn a living helping others plan their perfect trips.

Today, HawaiiGuide continues to evolve. From interactive trip planners to AI-driven concierge tools, we’re always looking for new ways to help travelers experience Hawaii in the most meaningful way possible. But at its core, our mission remains the same: to share the wonder of these islands, to inspire awe and respect for their beauty, and to ensure that every visitor walks away with a deeper appreciation for Hawaii than when they arrived.

Hawaii changed our lives. We hope, in some small way, Hawaii Guide helps it change yours, too.

– John & Victoria Derrick
Founders, HawaiiGuide

Into the cradle of Wai'ale'ale

Once-in-a-lifetime adventure...

In 2012, I had the rare opportunity to embark on a journey deep into the heart of Waiʻaleʻale Crater, a place so sacred and remote that few ever reach it. I had asked my guide for a once-in-a-lifetime adventure, and he delivered—taking me on an incredibly technical trek to touch the 5-million-year-old exposed rock at the back wall, where the Wailua Headwaters begin. Standing in that ancient, rain-soaked amphitheater—one of the wettest places on Earth—was the most profound experience of my life. While I can’t recommend others attempt it, the moment was a humbling reminder of Hawaii’s raw power and beauty.