If I had a quarter for every time someone told me that I just "had" to hike Diamond Head, I'd have enough money to buy myself a slice of pizza. Depending on where I got the pizza, it might be more enjoyable than hiking Diamond Head.
It was admittedly kind of neat. Diamond Head is essentially a huge hollowed out volcanic "tuff cone", built by the US army as part of their coastal artillery defense system. You have to see the cross-section drawing in the brochure to believe it. The entire inside of the hill is a labyrinth of hallways, artillery batteries, and observation posts. An impressive piece of work considering that construction was completed before 1911!
At the very top of the grueling, steep 0.8 mile hike is an observation tower, which commands impressive 360 degree views, of the harbor, the ocean, and the fungus-like sprawl of buildings that is Honolulu. We were warned to leave early, because it gets hot. Does it ever. At 8am on a September morning we were sweating like pigs and inhaling our water bottles. I don't know what it is about volcanic rock and moist, dark, concrete tunnels, but it makes a girl sweat. I mean glow. Right. Bring plenty of water if you go, and if you're at all frightened of the dark or dark tunnels, bring a flashlight, although you will only be in total darkness for a few seconds without one.
Bird lovers should bring their binoculars, because the grounds of Diamond Head State Monument are crawling with Golden Plovers, Brazilian Cardinals, doves, and countless other specimens. There are helpful signs at the entrance with a photo and description of each species, so you can easily identify which ones you saw.
The gate to Diamond Head Road is locked from 6pm to 6am daily. That should give you an idea of how early you can start your hike (or jog, if you're looking for a fantastic workout!)
Getting there: from Waikiki, take Kalakaua Avenue East. It merges with Diamond Head Road just outside of town. Make a left on Monsarrat Avenue. From there you can follow signs to the parking area. Allow an hour to an hour and a half for the hike, depending on your fitness level and how many photos you plan to take at the top! Entrance $1 pp.