Oahu is the perfect mix of urban and island life and the gateway to the history, culture, food and natural beauty of the Hawaiian Islands. For history and cultural buffs, you will enjoy visits to Pearl Harbor, the state Capitol, Iolani Palace and other historical landmarks. For foodies and party goers, Oahu has the most restaurants, waterholes and clubs of any other Hawaiian island. For nature lovers, there are miles of pristine beaches and hiking trails to explore, tons of golf courses and kayak opportunities. For surfing addicts, come in December to March where you may catch 20+ feet monster waves on Oahu’s famed North Shore.
What to do:
Day 1 (Waikiki and Downtown Honolulu) - Arrive, pick up rental car (a necessity in Hawaii!), get and settle in.
In downtown Honolulu, you will find Iolani Palace, the only royal palace in the U.S., the Supreme Court of Hawaii with the golden statue of King Kamehameha in front, State Capitol with the statue of St. Damien and the Eternal Flame to commemorate the service men of Hawaii, Kawaiahao Church, the Westminister Abbey of Hawaii, and Honolulu City Hall (best during its annual Christmas lights and sculptures show). They are all in one strip on King Street, so it’s easy to hit all of them on a casual stroll. Break for lunch. Drive to the Roundtop for panoramic views of Honolulu.
Depending on the time you get in, you may be able to squeeze in a 30-minute hike up to the summit of Diamond Head for gorgeous, panoramic views of world-famous Waikiki Beach, the iconic, crescent-shaped beach of Hawaii. Take a leisurely stroll through the Waikiki beachfront towards Ala Moana, popping into cute souvenir shops that dot the main drag of Kalakaua Ave or pop your towel down on a section of the beach whenever you get tired. The sand behind the Moana Surfrider Hotel is so fine that you won’t be able to stop digging your toes into the finest white powder ever, or try Kahanamoku Beach, a peaceful lagoon, on the beachside of the Hilton Hawaiian Village. If you want to try out surfing, surfboard rentals and surfing lessons are offered right on the beach. Stop for happy hour/sunset drinks on the beachfront or in an ocean cruise, followed by dinner at one of the numerous options in Waikiki. If you are artistically inclined, art galleries open their doors for an evening of gallery walks around historic Chinatown on the first friday of each month.
Day 2 (East Oahu) - Snorkel at Hanauma Bay for half a day (open everyday except Tuesdays). Be sure to get there by 8am or 8:30am because 1) the parking lot will be full by 9 or 10 am and you will have to park really far away, and 2) the water is clearer early in the morning so you will be able to see more fish. You can buy your own or rent snorkeling gear at the beach.
Take lunch break at Koko Marina Shopping Center, where Kona Brewing Company serves up a delicious pint of coconut-flavored locally-brewed beer. Drive east along the picturesque Kalanianaole Highway towards the Halona Blowhole, where you will love the spray of the ocean mist on your face as the water squirts out in a glorious gush and spills onto the rocks. DO NOT go over the guardrails near the blowhole itself as the rocks can be slippery. Next to the blowhole, there’s a romantic little hidden gem of a beach dubbed the Eternity Beach where the movie, From Here to Eternity, was shot. Hike a few short steps down to the small, secluded beach and you will be the envy of all the blowhole onlookers. Continue to drive to Sandy’s Beach for top-notch waves and join in the boogie boarders! But watch for surf advisory signs as the waves at Sandy’s are extremely strong, so tighten that swim suit! Also a great spot to fly kites as the wind is very strong here. Alternatively, if you’ve had enough water for the day, hike the 1000+ stairs straight up Koko Head Crater for sunset views of East Oahu.
Day 3 (Kailua and Kaneohe) - Drive east along Kalanianaole Highway and do an easy, morning hike to Makapu’u Light House for rewarding views and possible humpback whale sightings from December to March. Enjoy the spectacular Koolau mountain range on your left and the gorgeous beaches on your right as you drive towards Waimanalo Beach, Bellows Beach Park, or Kailua Beach Park, all family-friendly beaches with pine tree shades, showers and picnic areas. If you see a sign for “Huli-Huli Chicken” on the roadside, do stop and thank your lucky stars that the stand is open. Best BBQ chicken ever--Hawaiian style. After you are delightfully fed, you will be ready to hit Lanikai Beach, the most beautiful beach on Oahu--or anywhere for that matters--where two small islets, Moku Nui and Moku Iki, juts out from aqua blue waters in the background. You can rent a kayak to get to these islets or rent a SUP (stand up paddleboard) to enjoy the calm blue waters. Stop for lunch in Kailua Town where there are tons of restaurants serving anything from fish tacos to burgers or plate lunch, a local favorite. On the drive back, visit the Pali Lookout for spectacular views of Kailua and Kaneohea (bring for jacket for the gusty Pacific winds up there).
Day 4 (Pearl Harbor and North Shore) - Visit Pearl Harbor to witness first-hand the destruction that lead to America joining World War II and the US Missouri Battleship to see the kind of big gun that helped America to win the fight.
Drive to Haleiwa, a quaint surfer town on Oahu’s North Shore. Get shave ice at Matsumoto’s, a local favorite for the better half of the last century. Get a late lunch at one of the famous shrimp trucks on the north shore: Giovanni’s or Fumi’s. In the winter months, check out monster waves at Pipeline Bonzai or Sunset Beach and try to attend one of the pipeline surfing competitions come November to December. Reserve the afternoon for golf, either at the ritzy Turtle Bay Golf Course or the cheap, local alternative, Kahuku Golf Course, which has equally nice ocean views for a fraction of the price.
Hike through the tropical rainforest for the opportunity to splash into a tropical waterfall at Manoa Falls or Maunawili Falls.
For shoppers, check out Ala Moana Shopping Center, the biggest outdoor shopping mall in the world and just next door to Waikiki, Waikele Outlet Mall for name-brand bargains, and Aloha Stadium for cheap souvenirs on swap meet days on Wednesdays and weekends. For families with kids, Sea Life Park, which offers dolphin shows, is across the street and is great for kids. For adventurers, Makapu’u Beach Park offers paragliding lessons.
Eat & drink:
Lunch - Nico’s Pier 38 for seafood, Kaka’ako Kitchen for gourmet plate lunch, Helena’s Hawaiian Food for haupia, lomi lomi salmon, poke, and kalua pork, Wailoa Shave Ice for shave ice ((my favorite flavor is rainbow with mochi balls, ice cream, and condensed milk) and spam musubi, breakfast at Koko Head Cafe. Leonard’s for malasadas or portuguese donuts.Yakiniku Hiroshi (Japanese BBQ). Aracino (Italian). Addiction, the nightclub located at The Modern Honolulu (smart casual dress code).
Get on a 30-minute interisland flight on Hawaiian Airlines to the Big Island, either to the Kona-Kailua Airport or the Hilo Airport. Expect to pay around $100 one way.
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