This luxe neighborhood surrounding the iconic mountain of Diamond Head boasts palatial oceanfront homes, scenic lookout points and wide avenues.
The Waikiki Natatorium War Memorial, the picturesque outdoor pool on the oceanside of Kapiolani Park, was opened in 1927 on the birthday of Olympic gold medalist swimmer and godfather of surf Duke Kahanamoku. Though it has been closed for 40 years, it was recently named a National Treasure.
Check the surf from the top of Diamond Head Road; then cruise over to Monsarrat for acai bowls at Da Cove Health Bar & Cafe (3045 Monsarrat Ave., #5, 732.8744, dacove.com) and bikinis from Diamond Head Beach House (3128 Monsarrat Ave., 737.8667, diamondheadbeachhouse.com). Espresso bar and art gallery Ars Cafe (3116 Monsarrat Ave., 734.7897, ars-cafe.com) is a perfect place to relax over avo toast and a cold brew.
The loop around Diamond Head is just under 4 miles and features stunning ocean views, plentiful water fountains and restroom facilities, making it an ideal route for walking, running and cycling.
Ala Moana/ Kapi'olani/ Mo'ili'ili
Hawai‘i boasts the world’s largest open-air shopping mall, Ala Moana Center (1450 Ala Moana Blvd., 955.9517, alamoanacenter.com). The shopping and dining mecca is constantly expanding and now offers ultraluxe residential condos.
“Magic Island” is not actually an island, but rather a man-made peninsula created in 1964 at Ala Moana Beach Park. Intended as the site of a later-scrapped resort complex, it is now used for outdoor recreation.
Pint + Jigger (1936 S. King St., 744.9593, pintandjigger.com) is one of Honolulu’s best-kept secrets, serving craft beers and signature cocktails in a cozy social-club atmosphere.
At Ala Moana Center, check out Shirokiya Japan Village Walk (Street Level 1, 973.9111) for authentic Japanese food and drinks in a setting made to look like a Japanese town. Hit the Lanai at Ala Moana Center for quick sips at Agave & Vine wine and tequila bar (Mall Level 2, agavevine.com) or delectable shave ice at Island Vintage Shave Ice (Mall Level 2, 942.7770).
Memorial Day draws a big crowd to Ala Moana Beach Park for the annual Shinnyo Lantern Floating Festival. The public releases floating wooden- framed lanterns onto the water in remembrance of lost loved ones, creating an unforgettable scene.
The hip urban area some call “O‘ahu’s Brooklyn” keeps on developing, with exciting construction projects as far as the eye can see. New high-rise buildings like the 60-acre Ward Village, home to Nobu and the South Shore Market, have transformed the area. The Neal S. Blaisdell Center (777 Ward Ave., 768.5400, blaisdellcenter.com), O‘ahu’s entertainment destination, sits between King Street and Kapi‘olani Avenue.
The Kaka’ako neighborhood has been transforming from a historically industrial zone to an up-and-coming cultural center thanks to Pow!Wow!, a Hawai‘i- based arts and music festival started in 2010. The organization aims to beautify cities through street art, so it began painting incredible murals that now attract visitors from all over the world.
The hip (and very Instagrammable) Australian-inspired coffee shop Arvo Café (324 Coral St., Ste. 1A-104B, 312.3979, arvocafe.com) recently reopened to a bigger spot in the SALT complex. Hit up the South Shore Market in Ward Village (1170 Auahi St., 591.8411) for locally-owned boutiques like Salvage Public, Mahina and Kealopiko that carry a great selection of curated island favorites. For upscale Hawaiian furnishings and decor, you can’t beat the selection at Martin & MacArthur (1200 Ala Moana Blvd., 591.1949, martinandmacarthur.com). Order the meat—any meat—from Butcher & Bird (324 Coral St., Ste. 207, 762.8095, butcherandbirdhi.com), a new butcher and deli in the SALT complex serving up some of the best burgers on the island. Upstairs from the Aloha Beer Company (700 Queen St., 544.1605, alohabeer.com) you’ll find exceptional craft.