A Diamond Head Hawaii Hike Is Fun for the Whole Family

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Looming large over downtown Waikiki is Diamond Head Hawaii. Hawaiians call the strange craggy outcropping at the edge of the beach Leahi—”the brow of the tuna”—for its dorsal fin shape. The path leading up the landmark to its summit edge and the surrounding area is ripe for exploring. It’s also one of the best hiking trails in Hawaii.

Diamond Head Hawaii is one of the few hiking trails near Waikiki that is moderately challenging with a vertical climb, but that is also fun and accessible for the whole family. The trail itself has winding staircases and mysterious concrete bunkers. From its base, you go back and forth up dusty, unpaved switchbacks, making a zigzag pattern as you rise ever higher up the crater rim.

Different parts of the hiking trail enter underground tunnels. These man-made caves were built in 1908 to secretly reach the bunkers at the summit that served as lookouts and artillery stations. The end of one tunnel leads to a 43-step spiral staircase just before the summit. But then, just when you think you’ve arrived, there’s a fork, forcing you to choose your own adventure to the top. Not your average hiking trail, Diamond Head Hawaii includes both natural and man-made elements that keep you on your toes.

From the top, there are sweeping views of downtown Honolulu. On a clear day, you can even see the other side of the Island and its distant coastal Waianae Mountains. The elevated vantage also makes it easy to see that this is not a mountain at all. Instead, it’s a circular ridge enclosing a long-extinct volcanic crater! Be sure to pause and take in the 360-degree views. If you’re really lucky and you make the climb between November and April, you could even spot breaching humpback whales offshore during their winter visit to Hawaii’s warm waters.

It may be tempting to reward your efforts and commemorate the day with one of the certificates of achievement sometimes offered for a donation at the summit, but be aware that the only licensed outlet, whose funds support the park, is at the kiosk near the trailhead.

After all that hiking, you will have certainly built up an appetite. If you’re making the climb on a Saturday, head to the sprawling Farmer’s Market at Kapiolani Community College first and pack a picnic, or score a healthy snack after your adventure. Otherwise, head straight to Diamond Head Market & Grill post-hike for ‘ono grinds—they serve some killer banana pancakes at breakfast, and gourmet plate lunches the rest of the day. You’re sure to find something for everyone in the family, just remember to save room for dessert from their bakery!

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