Diamond Head really does have it all. The cozy oceanfront neighborhood has the eponymous Crater and Monument, Diamond Head Beach Park, the thriving commercial strip of Kapahulu Ave., the Ala Wai Golf Course, and the Wa‘ahila Ridge hiking trail. Plus, the ‘hood shares borders with both the uber-upscale residential streets of Kahala and foodie-favorite Waialae Ave. in Kaimuki. Residents enjoy easy access to Kapi‘olani Park (walkable and bikeable from many parts of the neighborhood) and the quieter beaches on the edge of Waikiki.
1. WHAT TO EXPECT
Nearly everything a person might desire can be found here, from ocean to jungle, outdoor sports to boutique gyms, quick plate lunch to five star dining. Expect a lot—you’ll find it!
2. THE LIFESTYLE
Laid back and friendly: peak South Shore style.
3. WHAT NOT TO EXPECT
Deep jungle or full-on urbanity: Diamond Head is, in many ways, the perfect compromise between North Shore and town, with enough buzz to be exciting but not so much as to overwhelm. That said, the beach and the hikes are never empty of other people, and to do serious business (or, for many folks, to commute to the office) you’ll likely have to take a drive downtown.
4. THE MARKET
Condos and single family homes, with smaller apartment buildings near the ocean, historic palatial mansions tucked away on some of the backroads, and a block of adorable historic oceanfront French Tudors that have barely changed hands since the 1970s.
5. YOU’LL FALL IN LOVE WITH
The cafes and lunch spots. Between world-renowned Ono Seafood, sophisticated Ars Cafe, and quirky yummy Pioneer Saloon, some of the best casual restos on O‘ahu can be found right in this ‘hood.
Hip, Low-key, Pricey, Classic South Shore, Down to Earth, Quiet & Serene, Parks & Recreation, For Foodies, Waterfront Views, Great Outdoor Spaces
Airport: 30m by car
Downtown: 15m by car
Diamond Head: 0m by car
North Shore: 1hr by car
Kapolei: 45m by car
East to West Palolo Ave. and Alohea St. to Manoa Stream and Koali Rd.
North to South Wa‘ahila Ridge State Rec Area to Ocean
Nearby Neighborhoods Kahala, Waikiki, Kaimuki, Manoa
Named Lēʻahi in Hawaiian (which roughly translates to “brow of the tuna”) for its resemblance to the dorsal fin of the ahi, the neighborhood’s eponymous crater was dubbed “Diamond Head” by confused British sailors who, upon arrival in the 1800s, mistook the sparkling calcite crystals for diamonds.
Close to both Waikiki and downtown Honolulu, Diamond Head is super convenient and feels small despite its many amenities. This is the kind of nabe where most folks have a regular lunch spot and coffee bar, and sprawling Kapi‘olani Park is host to all kinds of leisure and athletic activities.
Diamond Head is a little bit younger and hipper than elegant Kahala, but this is definitely still an upscale neighborhood, as evidenced by the historic architecture and genteel street life.
Residents tend to live quiet, community-oriented lives, patronizing the local restaurants and shops, frequenting the beaches and parks, and steering clear of the tourist-heavy crater hike, which is as crowded as it is beautiful.
Living the outdoor lifestyle is beyond easy in Diamond Head, where it is possible to walk to the beach from many points for a surf or swim. The Diamond Head Loop is a favorite for runners, with free outdoor gym equipment as well as bathrooms and water fountains along the path.
Kiddos (and parents) appreciate easy access to calm Kaimana Beach, Waikiki Aquarium, and the wonderful Honolulu Zoo.
Tourists and residents alike line up for the popular healthy-ish sweet treat options on Monsarrat Ave: real-fruit shave ice at Monsarrat Shave Ice, açai bowls at Da Cove Health Bar, and banana “nice cream” at the Banán truck.
Because it so perfectly splits the difference between small town vibes and big city feel, Diamond Head is lacking in things like big box stores and late nightlife on the one side, and remote wilderness jungle on the other. For many residents, that is the point, but if solo hiking or fast access to Costco are desired, you’ll want to look elsewhere.
Midpriced condos turn over fairly regularly on sweet cul-de-sacs and roundabouts like Pualei Circle, which is just a block from the “main drag” of Monsarrat Ave but feels private and tucked away.
The cafes and lunch spots. Between world-renowned Ono Seafood, sophisticated Ars Cafe, and quirky-yummy Pioneer Saloon, some of the best casual restos on O‘ahu can be found right in this ‘hood.
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