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How to Spend a Week on Oahu, Hawaii

Updated: Dec 2, 2022

The Gypsea Traveller is a Hawaii Travel Agency. The Owner, Libbi is a travel agent that lives in Hawaii. she has visited all of the Hawaiian Islands and lives on Oahu. This blog has a ton of recommendations based on first hand experience living in Hawaii.


Getting off the airplane in Honolulu and heading to a hotel in Waikiki can be overwhelming if it's your first time on the island. Waikiki is definitely not the Hawaii most tourists expect and many will leave the island feeling like they didn't get the true Hawaiian island experience.


I have. been living on Oahu for 6 years and enjoy taking my friends and family around the island to experience what Oahu can offer them. Below I have a day to day itinerary for how I'd recommend you spend a week on Oahu, Hawaii.


Day 1: For your first day on Oahu, I'd recommend staying in Waikiki.


There are many beaches in Waikiki, but my two favorites are Queen's Beach and Kaimana Beach.


Queen's Beach is right in front of the Honolulu Zoo and has the pier to the right of it. I recommend staying on the left side of the pier. If you want to try boogie boarding, this spot has great mini waves to experience boogie boarding. Just be careful of the coral as the water is shallow and the coral can cut you as you boogie board.


Kaimana Beach is to the left of Queen's Beach. From Queen's Beach, walk left to the aquarium. Walk past the aquarium and to the left side of the war memorial is Kaimana Beach. I just found this beach the last time I was on Oahu and really loved it as it had nice shallow water and no large waves. The beach is not too busy and has restaurants and a hotel store near it for snacks and drinks.


When you get warm from sitting on the beach, check out Vintage Island Shave Ice. It is located by the Cheesecake factory on Kalakaua St in Waikiki. It’s amazing. They use natural flavors for the shave ice. My favorite was the Lilikoi. Make sure you get ice cream on the bottom and sweetened condensed milk on top!!!


If you’re there on a Friday, Waikiki has Friday Night Fireworks that you can experience from the beach in Waikiki.

(The view from the MaiTai Catamaran is amazing)

Day 2: Experience the East side of Oahu


Before you head out for the day, I recommend starting your day by eating breakfast at Cinnamon’s in Waikiki. The french toast is amazing as well as their Red Velvet Pancakes. They also have Mac Nut Pancakes and Guava Pancakes. Our new favorite spot for breakfast is Sweet E's Cafe. You'll need a car to get there but it's only a five minute drive from Waikiki. Again, their french toast is to die for!


Once you're done put Makapu'u Lookout into your GPS to get out of Waikiki.

If you want to snorkel while you're on Oahu, check out Hanauma Bay. You'll need to make reservations and pay $25 for each adult, but the snorkeling there is great.

(Hanauma Bay)


Once you're done snorkeling drive to Halona Blowhole.The waves hit the cliff and go under the rocks, then come up through the hole making it look like a whale blowhole.


Next drive to Makapu'u lighthouse. There is a hike at the lighthouse or you can opt for the amazing viewpoint of Bird Island and Sea Life Park.


You'll be tired your first night so hang out at the resort, grab some food and go to bed early.

(The view from Makapu'u Lookout)


Day 3: Drive to the North Shore.


From Waikiki you will want to put the Dole Pineapple Plantation into your GPS. The GSP will help you get on H1 out of Waikiki where you will take H2 to the North Shore.


1. The first stop on the way to the North Shore is the Dole Pineapple Plantation. You can walk around the grounds, jump on their train, walk through the pineapple maze and grab a dole pineapple ice cream. If you don't have children, you can skip this stop if you want, but it's sometimes nice to see.

2. Next, drive to Haleiwa town. There are some cute shops and restaurants in town. The Sand People is my favorite store. It has really cute ocean themed products and jewelry. If you're craving shaved ice, Matsumoto's Shave Ice is in Haliewa. It's a very popular stop, but after eating at Vintage Island Shaved Ice, it's just not the same!


4. Next head to Waimea Bay. This is the famous beach where all the surf competitions happen and you might spot a professional surfer if you're lucky. After that, you can drive to Banzai Pipeline Beach and Sunset Beach. These are local surf spots and are also famous for many surf competitions. I don't recommend swimming on the North Shore if the waves are big. Summer is usually the best time to swim on the North Shore.


5. When you start to get hungry, get back in your car, and drive back to Haliewa. there are multiple food trucks there.


6. To get back to Waikiki you will want to keep driving East around the island towards Kailua and Waikiki to do the North Shore Circle. You can always double back and go back the way you came, but I like doing the full circle. Make sure you’re not coming back from Kailua to Waikiki during rush hour as it can be busy!


If you'd like to see the North Shore by an Island Tour, check out the following excursions below:

Grand Circle Island Tour- Deluxe

Hidden Gems of Oahu

Private Oahu Circle Island Tour

Oahu + North Shore Tour

Day 4: If you have time check out Kailua on the Eastside of Oahu.

1. Drive to Kailua from the Westside or Waikiki and hike the Lanikai Pill Boxes. Your GPS should take you near the trail where you can find parking, but the hike starts off Kaelepulu Dr.

(The top of Lanikai Pill Box Hike)


2. After hiking the Pillboxes we also reward ourselves with Cinnamons for Breakfast. If you didn’t eat there in Waikiki or loved it in Waikiki and want more of it their original spot is in Kailua.


3. After breakfast, check out Lanikai Beach. It can be windier as it's the Windward side of the island, but it’s a gorgeous beach. Be careful and watch out for signs for Jellyfish on the Eastside. We still go in the water when there are jellyfish warnings but there is a chance you could get stung.

(A view of the East Side/Windward side from the highway)

Day 5: Go to Pearl Harbor


1.Go to Pearl Harbor. You can do the tours below or do it yourself by getting a ticket to the USS Arizona 8 weeks in advance or showing up at 7:00am when the gates open to get in the standby line for the USS Arizona. Afterwards you can purchase tickets to the USS Missouri (the battleship) or USS Bowfin (the submarine) if you want to see additional things.

Beyond The Call- Pearl Harbor Tour

Call To Pearl Harbor Tour 6:30am

Call To Pearl Harbor Tour 9:00am

Island Tour + Pearl Harbor


2. Grab lunch at Restaurant 604. It's next to Pearl Harbor.


3. Check out the Aloha Stadium Market after Pearl Harbor. It's across the street/nearby from the Memorial and has a range of souvenirs at great prices.



Day 6: Kualoa Ranch


Check out Kualoa Ranch to see famous movie sites such as Jurrasic Park!

You can zipline, ATV, horseback ride and more at Kualoa Ranch. Links to the excursions are here.



Check out my list of Recommendations for Excursions on Oahu here.



If you've been dreaming of a Hawaiian vacation, but don't know where to start to plan your vacation, book your free 30 minute consultation with The Gypsea Traveller to learn more. Libbi can help you book a vacation package that includes your flight, the perfect resort for you, car rental or airport transfers and insurance. She can also custom design an itinerary for you based on excursion and restaurant recommendations.

Libbi lives in Hawaii and has visited all of the Hawaiian Islands. She loves helping clients book their dream vacation to the Hawaiian Islands. You can visit www.thegypseatraveller.com and click on "Schedule Consult" to choose a date/time to zoom with Libbi, The Gypsea Traveller




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