Frequented by visitors and treasured by kamaaina, the southeast neighborhoods of Diamond Head and Waikiki are two of Oahu’s most well known. The area is home to much of the island’s dining, nightlife, and shopping scenes. With the world-famous Leahi, or Diamond in the background, Waikiki—meaning “sprouting water,” in Hawaiian—was once frequented by Hawaiian royalty. At the turn of the 20th century, it introduced Hawaii to the outside world when the Islands’ first hotel, the Moana Surfrider opened in 1901. Waikiki is now home to dozens of hotels, in addition to five-star restaurants, luxury shopping and family friendly attractions such as the Honolulu Zoo, the Waikiki Aquarium and Kapiolani Park. And the Diamond Head State Monument is one of Oahu’s most hiked trails on the island. Both remain iconic Oahu destinations, whether it’s your first visit to the island, or you were born and raised on Oahu.

Diamond Head State Monument
Diamond Head Crater is perhaps Hawaii’s most recognized and photographed landmark. It got its name from sailors who mistook the slope’s calcite crystals for diamonds. Hawaiians had their own name for the significant crater, calling it instead Leahi, meaning brow of the tuna. They thought the crater’s sharp slope looked like an ahi, or tuna fish head. Diamonds and fish heads aside, for many visitors, hiking the crater is a must do during a trip to Oahu. With a flat path most of the way—there are stairs near the top—it’s an easy-to-intermediate hike. But the views at the top make up for the lack of terrain diversity, and the crowds. Here you can see Waikiki and Honolulu as well as Koko Head Crater and the rolling waves of the ocean. On a clear day, you can even see the outlines of Maui and Molokai. Cori’s Tips: Start this popular hike early, and don’t forget water and sunscreen. This trail is sunny and hot.

Kalakaua Avenue
Waikiki’s Kalakaua Avenue provides an introduction to the thousands of first-time visitors to Oahu. The bustling avenue, with its long stretch of beach, is dotted with sophisticated resorts, each with its own microcosm of shopping and dining. The area launched tourism in Hawaii. In fact, tourism is still the No. 1 driver of the economy today. The avenue is named after the monarch, King David Kalakaua. Known as the Merrie Monarch, King Kalakaua had a passion for music, hula and festivities. (The annual hula competition in Hilo, aptly named the Merrie Monarch, is in honor of him.) If you’re looking for some high-end retail therapy, look no further than Kalakaua Avenue! The Luxury Row featuring stores such as Tiffany & Co., Coach, Gucci, Yves Saint Laurent and Chanel. There’s duty-free shopping at T Galleria. The Royal Hawaiian Center and the Waikiki Beach Walk each feature upscale local boutiques, national brands and restaurants. The newly redeveloped International Market Place, a Waikiki shopping institution first opened in the 1960s now has high-end shops and dining.