Travel Itinerary | 5 Days on Oahu

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All photography by @studioist.

The island of Oahu—home to roughly two-thirds of the population of the state of Hawaii.

Known as "The Gathering Place," Oahu is also home to the state's capital, largest city, and deepawater marine port, Honolulu.

Honolulu and the world-famous Waikiki Beach has been a place of gathering for the monarchs of the Hawaiian Kingdom and their spot of choice for surfing.

Pearl Harbor, a lagoon harbor on the west side of the capital, remains an active military base and the site of the attack by the Empire of Japan in 1941, which lead the U.S. to enter World War I.

Whether you're interested in relaxing beach time, surfing, snorkeling, hiking, biking, sailing, museums, history...Oahu has it all! Hopefully this itinerary will help you make the most of your time on this enchanting island.

Also check out our Travel Guide: Oahu for a guide to some of the best activities, food, and beaches on the island.

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Aloha (hello)!

Relax you’re in Hawaii! Depending on what time your flight arrives, check in to your hotel, freshen up, and settle in to “island time.”

4:30 P.M. — Get dressed for dinner and to the world-famous Waikiki Beach. A short stroll with your toes in the sand will get you in the Aloha spirit. Watch some surfers, admire Diamond Head, and take in the sights and sounds of the busiest beach in Hawaii.

6 P.M. — Grab dinner in Waikiki, preferably somewhere with a lanai (porch) and potentially sunset views.

8 P.M. — After dinner, stroll along the always busting strip. Watch some street performers, do some window shopping, and of course some people watching. Maybe some dessert - check out MoDo or get some shave ice - along the way as well. :)

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Let’s Get Physical!

7 A.M. — The time change will probably have you waking up quite early so take advantage of it. Grab a coffee and some breakfast in Waikiki, perhaps at Olive & Oliver inside the Surfjack Hotel (412 Lewers Street, Honolulu) or ARS Cafe Gallery at the base of Diamond Head (3116 Monsarrat Avenue, Honolulu).

8 A.M. — Drive to and hike the Diamond Head State Monument. It’s not the most dramatic or unique hike on the island, but the stunning views of the coast and city of Honolulu along with the military history make it a memorable hike. The trail to the summit has stair sections which climb dramatically in elevation, yet there were people of all shapes, sizes, and fitness levels completing the climb. Entry is $5 per car or $1 per person if you walk in on foot.

11 A.M. — Grab lunch on the way back to or when you’re back in Waikiki. If you arrive around 11 a.m. you’ll beat the lunch rush at Marukame Udon. (see n1 below)

1 P.M. — Change and sunscreen-up for an afternoon at Waikiki Beach. Rent a board (and an instructor if you’re a beginner) and surf one of the world’s most famous beaches. I’d recommend giving surfing a go early on that way if you enjoy it you’ll have time to try it a few more times before the end of your trip.

7 P.M. — Surfing is tiring so don’t feel bad if you are beat today. Shower and head for dinner, drinks, and dessert in Waikiki, perhaps Hideout at The Laylow. Getchu some of ‘dat Huli Huli Chicken. Yum!


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The North Shore

8 A.M. —Gotta fuel up for a big day. Try Sweet E’s Cafe or Island Vintage Coffee.

9:30 A.M. — Try and arrive as the Dole Plantation opens to avoid the crowds and beat the heat. Learn about pineapple production and plantation life for immigrants on Oahu. Don't forget to try the world-famous, sought-after Dole Whip for a refreshing treat bursting with flavor.

11:30 P.M. — Walk around the charming surf town of Haleiwa (pronounced hah-lay-EE-wah). Check out the cute boutiques, art galleries, and crazy long line at Matsumoto Shave Ice before or after grabbing lunch. We’d recommend Beet Box Cafe or Haleiwa Bowls.

1 P.M. — Head to the Polynesian Cultural Center. Explore the Hukilau Marketplace and village reconstructions, attend the afternoon cultural presentations and activities, then evening dinner, luau, and show.

9:15 P.M. — Drive back to Waikiki

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The Windward Side

8 A.M. — Grab some breakfast at Hula Grill, located at the Outrigger Waikiki Beach Resort (2335 Kalakaua Ave Ste 203, Honolulu) and coffee at the Honolulu Coffee Experience Center (1800 Kalakaua Avenue, Honolulu) or one of their shops like the one in the Moana Surfrider.

10-ish A.M. — Tour of Kualoa Ranch. Whether you tour the 4,000-acre property on ATVs, horseback, jeeps, or e-bike, you’ll see filming locations from tons of Hollywood movies. Most tours run 90-minutes, but if you do multiple activities you’ll have to adjust the schedule for the rest of the day.

1 P.M. — Grab lunch at one of the many food trucks or roadside stands, stopping to enjoy it on one of the several beaches along the coast, like Lanikai Beach or Sandy Beach.

3 P.M. — Snorkel at Hanauma Bay Nature Preserve. By this point in the afternoon, you’ve missed the bus tours and morning crowds. Relax in the shade of a beach-side palm tree and snorkel with tropical marine life, shielded by the cove from rough ocean conditions.

7 P.M. — Congrats! Now you’ve driven around the windward side of the island and through the center. This evening, grab dinner close by like Yauatcha in International Marketplace (2330 Kalakaua Ave, Honolulu) for dim sum deliciousness or Waikiki Yokocho Gourmet Alley, the japanese food hall in the basement of Waikiki Shopping Plaza. If you eat somewhere else…that’s fine, just make sure to end the matcha parfait at Nana’s Green Tea. YUM!

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Aloha (goodbye).

8:30 A.M. — Eat at one of the brekkie places you didn’t get to yet or one you wanted to revisit.

10 A.M. — ‘Iolani Palace (optional). By this point in our trip we were pretty burnt, despite constantly applying sunscreen, so we enjoyed having an indoor activity, but if you are a big-time beach person by all means, head to the beach.

12 P.M. — Lunch is up to you. If you want to grab something and enjoy it at the park, try the Ala Moana Center. Inside there are tons of food options and shopping so you can grab some food, eat at the beachside park across the street, then get a little more shopping in before your flight. Or if you're not into shopping, simply enjoy your free afternoon at Ala Moana Beach Park.

 
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OPTIONAL EVENING ACTIVITIES

Friday Night Fireworks
Address: 2005 Kalia Rd, Honolulu, HI 96815
Every Friday night fireworks are shot from the Hilton Hawaiian Village. You can purchase tickets to watch from the Hilton’s pool or you can watch from the beach for free.

Twilight Tours at the Honolulu Zoo
@thehonoluluzoo | Address: 151 Kapahulu Ave, Honolulu, HI 96815
Every Friday and Saturday evening, the Honolulu Zoo hosts 2-hour Twilight Tours starting at 5:30 p.m.

ARTafterDark
@honolulumuseum | Address: 900 S Beretania St, Honolulu, HI 96814 The last Friday of each month from January through October, the Honolulu Museum of Art hosts a themed evening of entertainment, drinks, food and of course art!

Eat the Street
@eatthestreet | Address: 102 Ohe Street, Honolulu, HI
On the last Friday of each month, more than 40 food vendors set up at Kaka’ako Waterfront Park starting at 4 p.m. Dinner al fresco anyone?

Otherwise keep your eyes open. There are numerous “food truck” parks around the city on any given night, most with artisan vendors, live music, and touristy photo opportunities (aka get your picture taken with 10 tropical birds at once).

 
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n1. If you’re around on Tuesday or Saturday, check out Kapi’loni Community College (4303 Diamond Head Rd, Honolulu, HI 96816) known as the KCC, Farmer’s Market for produce, flower and food vendors.

n2. Hawaii has one of the lowest state tax rates so go ahead—buy that designer purse you saw on Kalakaua Avenue.

n3. Download the Shaka Guide through the app store and purchase the Oahu driving tour. This guide is an interesting way to pass the driving time and is filled with fun facts, history, island music, stories, and driving directions. You will have to adjust the tour since we’re following the path backwards. if you’re visiting another island, check the guide’s inventory as they have tours for other islands as well (the Road to Hana tour on Maui was very nice, just FYI).

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DID YOU TRY THE TAHITIAN COCONUT BREAD WHILE AT THE POLYNESIAN CULTURAL CENTER?

Well they shared their already vegan recipe and we adapted it to be gluten-free.

It's very simple to make, and is just as dense and sweet as the original. Check out the recipe here.