Kona, Hawaiʻi has been one of my favorite places to return to since 1998, and after visiting nearly every other year, it feels almost like a second home. Over time, my relationship with the Big Island has changed. Years ago, I experienced Kona while traveling with kids who later became teenagers — beach days, family activities, and the classic places everyone wants to see at least once. Now, I experience it in a different season of life, returning as a “free” adult with my wife, Gladys, discovering new places, new rhythms, and new ways to enjoy the island.

Even the familiar spots feel different now. Some of the classic places I visited years ago, I have returned to again — but the experience is not the same when life has changed, the company is different, and the pace is your own. Kona has a way of offering something new every time, whether it is a sunset that stops you in your tracks, a small beach you almost missed, a local pub where you truly feel the island spirit, or an underestimated little gem that becomes one of your favorite memories.

In this first Insider Notes piece, I’ll share personal observations, favorite experiences, and helpful tips from my most recent visit to the Big Island in October 2023. Gradually, I'll share all the practical tips from decades of visiting such a beautiful place.

Kona Through the Years

Before and Now: How Kona Changed With Me

What has made Kona even more special is how the island has changed with the different seasons of my life.

Before: Kona with Kids, Family, and the Classic Stops

In the earlier years, Kona was a family adventure. I visited with my children who eventually became teenagers, and the rhythm of the trip was very different. Back then, the focus was on the classic Big Island experiences: the places you want the kids to see, the beaches where everyone can play, the easy stops, the memorable drives, the “we have to do this at least once” activities, and, of course, keeping everybody fed, entertained, and not too sunburned.

Some of those classic spots I have visited more than once, but looking back, they never felt exactly the same. When you travel with kids, you see the island through their curiosity, their energy, and sometimes their impatience. A beautiful overlook becomes a snack break. A beach day becomes a full production. A scenic drive becomes a negotiation. And somehow, those moments become part of the charm.

My tip from those years: do not try to overpack the day. Kona is better when you leave room for the unexpected — a beach you did not plan to stop at, a shaved ice break, a sunset that makes everyone pause, or a simple meal after a long day in the sun.

Now: Kona with Gladys, New Adventures

My most recent visit in October 2023 felt very different in the best way. This time, I returned to Kona with my wife, Gladys, and the island opened up in a new way. We visited some of my favorite spots, yet found time to explore new places on the Island.

Even places I had visited before felt different because I was experiencing them with her. Kona has a way of doing that. The same ocean, the same lava rock, the same sunsets — but a completely new chapter.