Oahu is the third-largest island in the Hawaiian chain, and has the highest concentration of population, one of the reasons it is nicknamed “The Gathering Place.” It may be challenging to try to fit Oahu’s sights and activities into three days, but a well-planned itinerary provides an excellent introduction that will familiarize you with some of the island’s most popular attractions.
Day One Itinerary
A walking tour of historic Honolulu and nearby Chinatown is a marvelous way to familiarize yourself with Hawaii’s rich cultural heritage and fascinating history. Centered around Hawaii’s state capitol, the Capitol District includes the unique Iolani Palace, King Kamehameha Statue, Hawaii State Library and Kawaiahao Church. Honolulu’s Chinatown is one of the best in the nation, and you can get a taste of this area’s rich flavor by window shopping, stopping into several of the numerous art galleries, savoring the sights and sounds of the lively Asian markets (Oahu Market being the old-time favorite) and taking a break for a leisurely lunch (try one of the many Vietnamese pho restaurants). In recent years, Chinatown has undergone a transformation as the place for trendy restaurants, which are drawing locals back to downtown for memorable dinners. Among our favorites are The Pig & The Lady, Fete, HASR, Duc’s Bistro, Little Village, Livestock Tavern and JJ Dolan’s.
There are two ways to approach Oahu’s magnificent North Shore: The longer, slower route is along the Windward Coast, on Kalanianaole and Kamehameha highways, which meander from Makapuu and Waimanalo through the beach towns of Kaaawa, Punaluu, Laie and Kahuku, with a side trip to Kailua and Kaneohe if time permits. In the summer months, the ocean is calm and gentle; in the winter months, monster surf pounds the North Shore and surfers come from all over the world to take on the giant waves, some for fun, some for big cash prizes in professional contests. No matter what the season, save time to stroll through historic Haleiwa, a wonderful spot to dine, shop and explore some of the history that surrounds one of the world’s most famous beach towns, rich in surf culture. For a unique adventure, consider a glider ride at Dillingham Airfield, which provides a bird’s-eye view of the entire North Shore.
Reward yourself with some belly-up-in-the-sand time on Waikiki Beach. For the truly active who rise early eager to burn up some energy, a day exploring Waikiki could begin with a hike to the top of a dormant volcano. You can drive right into the crater of Diamond Head (admission charged), hike the easy trail to the crater’s top and enjoy an amazing panorama of Waikiki and Oahu’s entire south shore. Sights include the entire sweep of Waikiki Beach, Kapiolani Park, Honolulu Zoo, Diamond Head Lighthouse and Koko Head Crater in the eastern distance. Looking west, you’ll see the profile of the Waianae Mountain Range, at the opposite end of the island, highlighted by Mount Kaala, the highest point on the island. While you are on the beach in Waikiki, treat yourself to a sunset cocktail, dinner or just pupu (snacks) at the historic Moana Hotel, Duke’s in Waikiki or the Royal Hawaiian Hotel, the “Pink Palace” where celebrities have been propping up their feet since it opened in 1927.
Photos by Brett Uprichard; Shutterstock