From painted eucalyptus trees to secret surf coves, I explored four Hawaiian islands and learned exactly how to help travelers experience this extraordinary place.
Hawaii had been calling to me for years. As a travel advisor, I knew I needed to experience these islands myself, not just read about them in brochures or hear secondhand accounts. In 2023, my husband Dave and I finally made it happen. We flew into Honolulu, spent time exploring Oahu, then hopped on a cruise ship that carried us to Maui, the Big Island, and Kauai before returning us to where we started. Two other couples traveled with us, clients who became dear friends along the way.
What I discovered across those four islands changed everything I thought I knew about recommending Hawaii to my clients.
A Place You Cannot Understand Until You See It
The mountains stopped me in my tracks, over and over again. They have this extraordinary shape, almost like someone dragged their fingernails down the side of the rock, carving deep vertical crevices into the green. I kept trying to photograph them, but pictures never capture what your eyes see standing there. The Napali Coast, Waimea Canyon, these places have colors so vibrant they almost feel unreal.
One of our best decisions was purchasing a GPS app called Guide Along. We nicknamed him Jeeves because it felt like having a knowledgeable friend sitting in the backseat, anticipating our questions and pointing out spots we would have driven right past. Thanks to Jeeves, we found a deserted beach where a seal was sunning himself on the sand, completely unbothered by our presence. We discovered painted eucalyptus trees, which I did not even know existed until I stood beneath them, staring up at bark striped with greens, reds, and oranges.
The beaches alone could occupy weeks of exploration. Black sand on one stretch, then sugar powder brown on another, followed by pink and red. The sand itself varies from soft and fine to so thick it feels like walking through a snowdrift. And the water, while rough in many places, holds every shade of blue imaginable.
Climate Shifts That Feel Like Magic
What surprised me most was how dramatically the landscape changes as you drive. On the Big Island, you can start in Hilo surrounded by rainforest, lush and dripping with green, then drive to see an active volcano with mist and heat rising from the earth. Cross to the Kona side and suddenly you are in near desert conditions, gray and ashy, where you half expect tumbleweeds. Head into the mountains and you find yourself in ranch country with cattle grazing on green hillsides. All of this on one island.
We tackled the Road to Hana, and I now understand why people feel nervous about it. The winding route can be overwhelming, but having done it myself, I can walk my clients through exactly how to navigate it, where to stop, and what to expect. We found the best shave ice spots (and yes, it is shave ice, not shaved). The version with macadamia ice cream tucked inside is something special, nothing like the corner store treats back home.
Who Should Go, and Who Should Wait
Hawaii is perfect for independent travelers who do not need every moment choreographed. It works beautifully for couples, multigenerational families, and groups of friends willing to explore. If you crave adventure, want to see dramatic scenery, and enjoy driving through changing landscapes, this place will fill your heart.
But I will be honest with my clients: if you want to sit on a beach for a week at an all inclusive resort, save your money and head to the Caribbean. Hawaii is expensive. Accommodations, food, activities, it all adds up. This is a destination worth saving for, worth budgeting properly, and worth giving at least two weeks of your time.
Having walked those beaches, driven those winding roads, and stood in awe beneath those carved mountains, I can now share Hawaii with my clients in a way that feels personal and true. I know the timing tricks, the spring and fall sweet spots when weather cooperates and boats can safely venture out. I know the little nooks worth seeking out. And I cannot wait to help someone else fall in love with these islands the way I did.
Dave & Sonja
