Diamond Head Crater is one of the major landmarks on Oahu, and if you are nearby you should definitely spend a couple of hours to do this hike. The views from the top of the crater are AMAZING, and my son and I really enjoyed climbing through the tunnel and the old military bunker.
We wore hiking boots and shoes, but there were PLENTY of Japanese tourists hiking in flip flops. The trail is mostly paved, though there are a few places where the concrete is a little rocky. If you are a somewhat active person then you'll find this hike isn't that strenuous. However, if you are not in good physical condition, take your time and bring plenty of water.
When you get near the top of the crater there is a fork in the road. If you want to go through the military bunker then take the right fork and climb up the stairs (it looks like a lot of stairs!). On the way down take the paved trail.
The day we visited there was a food truck selling water, shaved ice, and snacks. We didn't try any of it but it is there if you need it.
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