Over the Rainbow: Your Hawaii Travel Guide

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Traveling to Hawaii was the fulfillment of a long-held dream. Join us as we share our favorite adventures, memories, and practical tips from the trip.

My Hawaiian dream began when I was a little girl. I remember sitting on the living room floor of our family farmhouse in Montana, the olive-green drapes pulled closed so the room was dark except for a bright rectangle on the popcorn-plastered wall.

That rectangle held one of my father’s slides. It was slide night at the Lynn house—Dad was showing photographs from his time in the US Navy during the Korean War.

Of all the images he showed, only one stole my breath: a perfect rainbow arching over a mountain with a lush garden in the foreground.

A rainbow. In Hawaii.

From that moment I decided I would go to Hawaii someday.


Fast-forward to a recent afternoon—Wednesday, April 17th, about 4:30 pm—and I wrote this in my journal:

I was seated in the open-air breezeway of Kahului Airport on Maui, the warm tropical breeze moving the palm fronds. Nearby, a young woman strummed a ukulele and sang a cheerful island tune. In an hour our plane would take us home, and I felt overwhelmed with gratitude. It still seemed unreal that I had finally stood in this place I had imagined for so long. The last day of a trip is always bittersweet; I wasn’t ready to leave.


For our final outing we had lunch at the Hula Grill on Kaanapali Beach.

The Hula Grill is an open-air beachfront restaurant where you can literally dangle your toes in the sand while you eat—one of those effortless island pleasures.

We were seated quickly—something of a small miracle on a busy day. As the hostess led us to a table right on the sand, a live musician was playing and singing, softly opening with, “Somewhere over the rainbow…” He added his own phrasing and warmth to the classic tune.

As I walked through the sand towards our table, he sang,

“Dreams really do come true…”

Hearing those words brought a lump to my throat. Behind my sunglasses my eyes filled with tears. I thought of my father’s slide and how, after all these years, this trip had become a true dream come true.

That very morning, while watching the day break at Napali Beach, the clouds gifted me with this:

A rainbow. In Hawaii.

When you dream about something for so long you sometimes worry reality will fall short of expectation. In our case, reality exceeded anything we had imagined. Each day on the islands offered new, joyful memories and small moments of wonder.

We noticed so many times how things seemed to fall into place—the chance to travel there in the first place, the scenery around every turn, and even small mercies that felt like protection when we made a bad choice (more on that later!).

Hawaii became a place where worries seemed to soften and drift away, a place where your troubles might just “melt like lemondrops.”


I’ll be taking a short detour from my usual home decor posts to document our time in Maui—and one day we spent in Oahu—here on the blog. I have dozens of photos and many small, meaningful details I don’t want to forget, so I’ll be sharing the days, the places we loved, and a few travel tips based on what we learned.

You’re welcome to follow along as Harbour Breeze goes Aloha!

My father’s original slide is on my desk now; it looks just as beautiful as I remembered. I tried to scan it to share here, but my scanner refused to cooperate that day.

We enjoyed the Hula Grill musician so much that we bought his CD. He performs under the name Da Barefoot Warrior, and the song “Over the Rainbow” was a highlight of our meal—gentle, sincere, and perfect for the moment.

Other posts from our Hawaii trip

  • The First Glimpse – Flying into Kahului
  • Visiting Upcountry Maui
  • Exploring Big Beach
  • Kaanapali Beach and Eating Hula Pie
  • Snorkel Trip to Molokini Crater and Discovering New Beaches
  • Day trip to Honolulu and Waikiki Beach
  • The Road to Hana
  • Things to Note when Traveling to Hawaii + The Highlight Reel Video