Over the Rainbow: Hawaii Travel Guide

Traveling to Hawaii was the trip of a lifetime for us. Follow along as we share our favorite adventures, memorable moments, and practical travel tips from our journey.

My Hawaiian dream began when I was a little girl, sitting on the living room floor of our Montana farmhouse. The olive green drapes were closed and the room was dark, except for a bright rectangle of light on the popcorn-textured wall. It was slide night, and my father was showing photos from his time in the Navy. Of all the images he shared, one stayed with me: a perfect rainbow arching above a mountain with a lush garden in the foreground.

A rainbow. In Hawaii.

From that single slide, a longing took root. Decades later, sitting in the warm, open breezeway of the Kahului Airport in Maui—palms swaying, kites dancing in the sky, and a young woman nearby strumming a ukulele—felt surreal. With an hour before our flight home, I wrote in my journal that I was overwhelmed with gratitude. The trip seemed like a dream realized.

We chose to end our vacation with lunch at the Hula Grill on Kaanapali Beach, an open-air restaurant where you can literally dine with your toes in the sand. We were seated after a surprisingly short wait and led to a beachfront table while a live musician sang a mellow rendition of “Somewhere Over the Rainbow.” He added his own lines and melody, and when he sang “Dreams really do come true,” I couldn’t help but get choked up. Through sunglasses my eyes filled with tears as that childhood image of my father’s slide came rushing back.

Just that morning at Napaili Beach, the clouds had gifted us with a rainbow—a small, private moment that felt like the fulfillment of that long-cherished dream.

There is a tendency when you’ve waited for something for a long time to expect reality to fall short. In our case, Hawaii exceeded every expectation. Each day on Maui—and our day in Oahu—was filled with new memories: sunrise light through the palm trees, unexpected kindnesses, and small moments that felt like answers to quiet prayers. We noticed countless details that seemed to fall into place: the logistics of getting there, the accommodations, the friendly people, and even gentle guidance when we made mistakes along the way.

Hawaii felt like a place where worries could melt away, where the pace encourages rest and reflection. We lounged in hammocks, watched the tide, and let the island’s rhythm slow us down.

For the next little while I’m taking a break from my usual home decor posts to document our days in Maui (and our day in Oahu) here. I want to preserve the details, share the sights and tips that helped make our trip so special, and give readers a sense of the island experiences that meant the most to us. Expect stories about beaches, local dining, scenic drives, and lessons learned while traveling.

I still have my father’s original slide on my desk; it’s every bit as beautiful as I remember. I intended to scan it, but my scanner chose that moment to be uncooperative. The memory of that small image, however, was with me on every path, beach, and overlook.

We also fell in love with a local musician who performed during our beachfront lunch. His music captured the spirit of the islands, and his version of “Over the Rainbow” is a memory I’ll carry home with me.

If you’re planning a trip to Hawaii, consider these highlights from our journey: exploring Kaanapali Beach, dining at seaside restaurants where you can feel the sand beneath your feet, waking early for quiet beach sunrises, and taking time to savor the slow, restorative pace of island life. Small details—like a friendly musician, a surprise rainbow, or the way sunlight filters through palm fronds—are what make the trip unforgettable.

Other posts about our Hawaii trip