Diamond Head
Friday, October 31, 2025
We grabbed the Waikiki Trolley in the morning and hopped off at Diamond Head. The plan was simple: look around, not hike it. When I looked up at the ridge, I said out loud, “Yeah, there’s no way I’m going all the way up there.” The driver claimed the hike was “about a half hour.” No chance — it’s longer, and I knew it.
We weren’t prepared for a hike at all — no water, no hats, no sunscreen. We figured we’d walk a little way up just to see how it felt. One step led to another, and with a few breaks along the way, suddenly we were much higher than expected. I kept thinking, If people older than me are doing this, I don’t have an excuse. At some point, we were committed.
We made it to the top, and the views were absolutely worth it. I was proud of myself. Going back down didn’t require as much cardio, but it was just as rough on the legs.
Along the way, I noticed couples hiking with babies strapped to their backs and even toddlers making the climb. It reminded me how different parenting looks these days — people don’t put adventures on pause just because they have kids.
We got back on the trolley and continued the historic tour through Honolulu, including a stop at Iolani Palace. As we rode, I found myself thinking about how much Oahu has changed — and keeps changing. Hawaiian Airlines had just flown its last flight under the HA callsign. The Alii Kai dinner cruise ship that I remember is now a vandalized husk. The International Marketplace went from open-air charm to a high-end mall. The Waikiki I first knew is gone, replaced by something shinier but not necessarily better.
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