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Perfect 3-day Oahu Itinerary

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

Oahu ItineraryA 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 and JJ Dolan’s.


Day Two

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.


Day Three

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.


Enrich your visit by participating in some of Oahu’s monthly Events and Special Deals.


Photos by Brett Uprichard; Shutterstock



  1. Kristal Goodwin

    I would love to experience the Hawaiian culture and spend time with the locals.
    What the cuisine is like and my favorite is spending time with locals to trule understand the way if life in Hawaii my dream vacation Always wanted to go there but a dream it has been maybe one day that dream will come true. What’s the most common dish a mother would make for comfort food?

  2. Dale Stenbeck

    Aloha…In July 2017, we spent 7 days on the Big Island then 7 days on Oahu. We did the amazing Island bus tour, two Kalua Pig (luau’s). , Pacific Air Museum, and wouldn’t leave without a visit to the Arizona Memorial and U.S.S. Missouri. We walked Waikiki every day and toured the zoo. We would love to revisit the Big Island to see the changes after the eruption of the volcano…Mt Kīlauea.

  3. Crystal Yeary

    Aloha Kristal, my name also Crystal. My dream was to go to Hawaii also so after our son’s was raised my husband and I went in 2017 and this September 2019 will be my 5th trip back. I fell in love for Maui we have been to all the Islands but Maui feels like home. It’s funny they say that the islands Choose You and I believe that completely because I fell in love with Maui at the airport. Sorry for going on and on what I wanted to tell you is I don’t know if you realize that you can make payments up to year on your airline tickets and some of the resorts you can also make payments on up to year so just on almost any budget if you really want to go you can find a way. I hope your dream comes true soon you won’t regret it I promise that. Mahalo

  4. Brett Uprichard

    The favorite dish a Hawaiian mother would make for comfort food would often be made with poi, the staple of the Hawaiian diet.

    Here’s an interesting quote that might inspire you:
    The size of your dreams must always exceed your current capacity to achieve them. If your dreams do not scare you, they are not big enough. 
~ Ellen Johnson Sirleaf


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