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Kapiolani Park, Diamond Head and Kapahulu

Hiking, shopping and eating in paradise
Rating: 5 out of 5 by EveryTrail members
Difficulty: Moderate
Length: 7.2 miles
Duration: Half day
Family Friendly

Overview :  Long before Waikiki became a tourism mecca, an adjacent 300-acre tract of land at the base of Diamond Head was set aside for a public ... more »

Tips:  If you’re into walking, you can tackle much of this itinerary on foot. Or you can find a metered parking space at Kapiolani Park and... more »

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Points of Interest

In its unique setting on Sans Souci Beach, the New Otani Kaimana Beach Hotel long has been celebrated for its superb ambience. Scottish author Robert Louis Stevenson wrote about the site, "If anyone desires such old fashion things as lovely scenery, quiet, pure air, clear sea water, good food and heavenly sunsets hung out before his eyes over the ... More

2. Diamond Head Road Lookout

You can work off your breakfast by strolling the two-mile walking path circling Kapiolani Park or tackle the one-mile uphill trek (via car or foot) along Diamond Head Road to the lookout for watching the early morning surf action. The former is a flat track with shade, restrooms and water fountains, while the latter is an uphill climb past the... More

3. Diamond Head State Monument

If you continue toward Koko Head from Diamond Head Lookout and take a left at Triangle Park, you'll find yourself on the backside of "Leahi" Crater on Diamond Head Road. On the left side is the parking lot for Diamond Head State Monument. The 0.8-mile hike from trail head to summit is steep and strenuous, gaining 560 feet as it ascends from the... More

On Saturday mornings, Kapiolani Community College campus is all abuzz with what's considered one of Oahu's top farmers' markets. Located just across Diamond Head Road from the lookout's parking lot, this food fest lets you mix and mingle with farmers and food producers who will tell you about their products, how they grow them and how you should... More

Busting at the seams with the world's largest selection of aloha shirts (more than 15,000), Bailey's Antiques and Aloha Shirts also shines with a wide selection of Americana and Hawaiiana antiques and collectibles.

Founded in 1980, the novelty emporium is chockfull of lighters (Zippos and Hawaiian), Hawaiian LPs, figurines, jewelry, sheet music, ... More

Rainbow's "onolicious" heaping mixed plate covers it all with barbecue meat, mahi mahi and boneless chicken--all served with two scoops of rice and macaroni salad for that carbo boost. Daily specials that tend to draw in the locals include roast pork with gravy, shoyu chicken and chicken long rice.
3308 Kanaina at Kapahulu Avenue
Phone:(808)... More

Both ONO and Rainbow Drive-In are easy walks from Bailey's. So no need to move your car from street parking on Kapahulu Avenue. Continuing mauka (toward the mountains) on Kapahulu, you can dive into an enormous Hawaiian-style plate lunch at Ono Hawaiian Foods too.

Both cater mostly to residents since they're off the beaten Waikiki path. But those... More

Chances are you'll be too stuffed from lunch to cap it off with dessert. But if you are jonzing for sweets, you're within walking distance of Waiola Bakery & Shave Ice Kapahulu. Akin to snow cones, these edible island icons run from basic with a flurry of sweet syrup flavors to more advanced with mochi, red azuki beans or ice cream as a base.
... More

You'll need to motor down Kapahulu to Leonard's. Here it's a ritual to order malasadas, a hole-free doughnut of sorts that's fried until the crust is golden brown with a light and fluffy inside.
933 Kapahulu Ave.
Address: 933 Kapahulu Avenue, Honolulu, HI 96816
Phone: 808-737-5591
Hours: Sunday through Thursday 5:30am - 9pm; Friday and... More